Acetic Acid → HCID 58980806, compound

HRID 1181376Notes

Reaction equation

HRID 1181376 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:19]([O:31][CH3:32])[CH:18]=1)=[O:15].[C:33](O)(=O)[CH3:34]>>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:14](=[O:15])[N:16]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]5[CH2:30][CH2:29][CH2:28][CH2:27]5)=[C:19]([O:31][CH3:32])[CH:18]=4)[C:33]([CH3:34])=[N:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 58980880HCID 58980880, compound

Product 1

HCID 58980806HCID 58980806, compound

Procedure

A mixture of 3-amino-5-(4-chlorophenyl)-N-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy) phenyl]thiophene-2-carboxamide and glacial acetic acid was refluxed overnight, concentrated to an amber viscous oil, triturated with water then filtered to give the title compound as its acetic acid salt as a tan solid (0.032 g, 64%). LCMS m/z 496 (MH+). 1H NMR (300 MHz, DMSO-d6) δ 8.35 (br, 1H), 8.00 (s, 1H), 7.95 (d, 2H), 7.55 (d, 2H), 7.20 (s, 1H), 7.10 (d, 1H), 6.95 (d, 1H), 4.20 (m, 2H), 3.75 (s, 3H), 2.75 (m, 2H), 2.55 (m, 4H), 2.20 (s, 3H), 2.00 (s, 3H), 1.65 (m, 4H) ppm.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationconcentrated to an amber viscous oil
  3. customtriturated with water
  4. filtrationthen filtered

Sources & evidence

ORD record
ord-1af26b584296457d801ee987525ceddc
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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