Hydrochloric Acid → HCID 16659659, compound

HRID 2097042Notes

Reaction equation

HRID 2097042 reaction equation
[CH3:1][N:2]([CH2:22][C:23]1[O:24][C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[C:27]=1[CH3:28])[C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[N:8][C:9]2[NH:18][C:17](=[O:19])[C@H:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[CH2:11][C:10]=2[CH:20]=1.[ClH:33]>C(Cl)Cl.C(OCC)C>[ClH:33].[CH3:1][N:2]([CH2:22][C:23]1[O:24][C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[C:27]=1[CH3:28])[C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[N:8][C:9]2[NH:18][C:17](=[O:19])[C@H:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[CH2:11][C:10]=2[CH:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16659660HCID 16659660, compound

Product 1

HCID 16659659HCID 16659659, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A stirring solution of (S)-(E)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(10-oxo-2,3,4,9,10,10a-hexahydro-1H-3a,8,9-triazabenzo[f]azulen-6-yl)acrylamide (0.235 g, 0.545 mmol) in CH2Cl2 (5 mL) under N2 was treated with anhydrous HCl (0.27 mL of a 2.0 M solution in diethyl ether, 0.54 mmol) After stirring for 18 h, the resulting solid was collected by filtration, washed with Et2O (100 mL) and dried to yield the title compound (0.22 g, 89%) as a yellow solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 12.15 (br s, 1H), 11.30 (br s, 1H), 8.87-8.83 (m, 1H), 8.36-8.31 (m, 1H), 7.63-7.55 (m, 2H), 7.50-7.48 (m, 1H), 7.35-7.22 (m, 3H), 5.07-4.95 (m, 2H), 4.47-4.26 (m, 3H), 3.63 (br s, 2H), 3.20-2.93 (m, 3H), 2.27 (s, 4H), 2.10 (br s, 1H), 1.88 (m, 2H); [α]25D +66.3° (c 0.90, methanol); MS (ESI) m/e 431 (M+H)+.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with Et2O (100 mL)
  3. customdried

Sources & evidence

ORD record
ord-53d720e9ba124bcd805c68c3766c40f3
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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