Acetyl chloride → 3-Amino-4-thiophen-2-yl-6,7-dihydro-5H-1-thia-6,8-diaza-s-indacene-2-carboxylic acid amide hydrochloride

HRID 2375362Notes

Reaction equation

HRID 2375362 reaction equation
C(OC([N:8]1[CH2:19][C:18]2[N:17]=[C:16]3[C:12]([C:13]([NH2:23])=[C:14]([C:20](=[O:22])[NH2:21])[S:15]3)=[C:11]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[C:10]=2[CH2:9]1)=O)(C)(C)C.C([Cl:32])(=O)C>CO>[ClH:32].[NH2:23][C:13]1[C:12]2[C:16](=[N:17][C:18]3[CH2:19][NH:8][CH2:9][C:10]=3[C:11]=2[C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[S:15][C:14]=1[C:20]([NH2:21])=[O:22]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 252056243-Amino-2-carbamoyl-4-thiophen-2-yl-5,7-dihydro-1-thia-6,8-diaza-s-indacene-6-carboxylic acid tert-butyl ester

Product 1

HCID 689136683-Amino-4-thiophen-2-yl-6,7-dihydro-5H-1-thia-6,8-diaza-s-indacene-2-carboxylic acid amide hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-amino-2-carbamoyl-4-thiophen-2-yl-5,7-dihydro-1-thia-6,8-diaza-s-indacene-6-carboxylic acid tert-butyl ester (4 g, 9.6 mmol)) in 70 ml of anhydrous methanol was added dropwise 7 ml of acetyl chloride under argon. The resulting mixture was stirred for 48 hours at room temperature. The solid was filtered and washed with methanol to give 3.14 g (93%) of the yellow product as its hydrochloride salt. 1H-NMR (300 MHz, DMSO-d6): δ 10.20 (brs, 2H), 7.96 (dd, J=1.2, 5.1 Hz, 1H), 7.36 (dd, J=1.2, 3.6 Hz, 1H), 7.32 (brs, 2H), 7.31 (dd, J=3.6, 5.1 Hz, 1H), 6.02 (brs, 2H), 4.63 (s, 2H), 4.42 (s, 2H). ES MS m/z 317 (M+H)+, 315 (M−H)−.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with methanol

Sources & evidence

ORD record
ord-1f3292bf6362456c9c55b0ec60fb8101
Source dataset
uspto-grants-2008_12
Patent number
US07465742B2

Reaction notes

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