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1,2-Dichloroethane → HCID 58646024, compound

HRID 1171895
Notes
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Reaction equation

HRID 1171895 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl.[N:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH2:38][NH:39][C:40]2[CH:44]=[CH:43][S:42][C:41]=2[C:45](O)=[O:46])=[CH:30][CH:29]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH2:38][NH:39][C:40]2[CH:44]=[CH:43][S:42][C:41]=2[C:45]([NH:1][C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][CH2:7][N:8]3[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=2)=[O:46])=[CH:30][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 21936857tert-Butyl 6-amino-2,3-dihydro-1H-indole-1-carboxylateHCID 68767362HCID 68767362, compound

Product 1

HCID 58646024HCID 58646024, compound

Reagents, catalysts & solvents

2
HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-aminoindoline-1-carboxylate (3.2 g, 13.68 mmol) in CH2Cl2 (135 mL) was added iPr2NEt (14 mL), 3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxylic acid hydrochloride (5.27 g, 16.42 mmol), EDC (3.93 g, 20.5 mmol), DMAP (0.81 g, 6.63 mmol), and HOAt (5.5 mL. 0.5M in DMF). The resulting mixture was then heated to reflux under N2 atmosphere. After 8 h the reaction was cooled to rt and then washed with 50% NaCl solution. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to yield a residue that was purified by silica gel chromatography (80% EtOAc in Hexanes 100% EtOAc) to yield tert-butyl 6-({[3-[(quinolin-4-ylmethyl)amino]thien-2-yl]carbonyl}amino)indoline-1-carboxylate as a yellow solid. MS (ES+): m/z 501 [M+1]. 1H NMR (d6-DMSO, 400 MHz): δ1.48 (s, 9H), 2.99 (t, J=8.4 Hz, 2H), 3.90 (t, J=8.4 Hz, 2H), 5.06 (d, J=6.0 Hz, 2H), 6.78 (brs, 1H), 7.07 (d, J=8.4 Hz, 1H), 7.40 (d, J=4.4 Hz, 1H), 7.56 (d, J=5.6 Hz, 1H), 7.66 (t, J=6.8 Hz, 1H), 7.78 (t, J=6.8 Hz, 1H), 8.04 (m, 2H), 8.21 (d, J=8.0 Hz, 1H), 8.82 (d, J=4.4 Hz, 1H), 9.35 (s, 1H).

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureto reflux under N2 atmosphere
  3. washwashed with 50% NaCl solution
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a residue that
  8. customwas purified by silica gel chromatography (80% EtOAc in Hexanes 100% EtOAc)

Sources & evidence

ORD record
ord-e1066bb4f6d947c39a0faa53480797d0
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07829717B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes