Triethylamine → HCID 178520164, compound

HRID 1443825Notes

Reaction equation

HRID 1443825 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH:22]=[C:21]2[C:17]([C:18](=[N:24][NH2:25])[C:19](=[O:23])[NH:20]2)=[C:16]([Br:26])[CH:15]=1)=[O:13].[O:27]1[C:31]2[CH:32]=[CH:33][C:34]([CH2:36][C:37](O)=[O:38])=[CH:35][C:30]=2[CH2:29][CH2:28]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH:22]=[C:21]2[C:17]([C:18](=[N:24][NH:25][C:37](=[O:38])[CH2:36][C:34]3[CH:33]=[CH:32][C:31]4[O:27][CH2:28][CH2:29][C:30]=4[CH:35]=3)[C:19](=[O:23])[NH:20]2)=[C:16]([Br:26])[CH:15]=1)=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27374552,3-Dihydro-5-benzofuranacetic acidHCID 178514327HCID 178514327, compound

Product 1

HCID 178520164HCID 178520164, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-4-Bromo-3-hydrazono-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid [3-(2-hydroxymethyl-pyrrolidin-1-yl)-propyl]-amide (0.22 g, 0.52 mmol) was added to a solution of (2,3-dihydro-benzofuran-5-yl)-acetic acid (0.93 g, 0.52 mmol), triethylamine (0.01 mL, 0.78 mmol) and HBTU (0.20 g, 0.52 mmol) in DMF (4 mL) and stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and purified by column chromatography (20% methanol in dichloromethane) followed by HPLC (10-100% acetonitrile/water) to give 0.040 g (13%) of (S)-4-bromo-3-[(2-2,3-dihydro-benzofuran-5-yl-acetyl)-hydrazono]-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid [3-(2-hydroxymethyl-pyrrolidin-1-yl)-propyl]-amide. 1H NMR (400 MHz, CD3OD) δ 7.75 (s, 1H), 7.37 (s, 1H), 7.24 (s, 1H), 7.11 (d, J=7.8 Hz, 1H), 6.65 (d, J=8.2 Hz, 1H), 4.50 (t, J=12.7 Hz, 2H), 4.10 (bs, 2H), 3.88 (dd, J=3.9 Hz, J=12.2 Hz, 1H), 3.74-3.40 (m, 6H), 3.22-3.04 (m, 4H), 2.26-1.81 (m, 6H). Mass spectrum (LCMS, ESI pos.): Calcd for C27H30BrN5O5: 584.46. Found 584.1; (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography (20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-58931af6e5e64d0eabb024449fdd661c
Source dataset
uspto-grants-2010_02
Patent number
US07662824B2

Reaction notes

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