Ammonia → 3-Amino-4-thiophen-2-yl-5,6,7,8-tetrahydro-1-thia-7,9-diaza-cyclopenta[b]naphthalene-2-carboxylic acid amide

HRID 2375365Notes

Reaction equation

HRID 2375365 reaction equation
C(OC([N:8]1[CH2:17][C:16]2[N:15]=[C:14]3[S:18][C:19]([C:22](=[O:24])[NH2:23])=[C:20]([NH2:21])[C:13]3=[C:12]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)(=O)C.N>CO>[NH2:21][C:20]1[C:13]2[C:14](=[N:15][C:16]3[CH2:17][NH:8][CH2:9][CH2:10][C:11]=3[C:12]=2[C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)[S:18][C:19]=1[C:22]([NH2:23])=[O:24]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6367Acetyl chlorideHCID 59854945HCID 59854945, compound

Product 1

HCID 598548663-Amino-4-thiophen-2-yl-5,6,7,8-tetrahydro-1-thia-7,9-diaza-cyclopenta[b]naphthalene-2-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 3-amino-2-carbamoyl-4-thiophen-2-yl-5,8-dihydro-6H-1-thia-7,9-diaza-cyclopenta[b]naphthalene-7-carboxylic acid tert-butyl ester (100 mg) in 10 ml of anhydrous methanol under argon 0.5 ml of acetyl chloride was added dropwise, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was neutralized with 7N ammonia in methanol and evaporated to dryness under vacuum. The residue was purified by silica gel column (chloroform/methanol, 30:1) to give a yellow solid. 1H-NMR (300 MHz, DMSO-d6): δ 7.88 (d, J=5.1 Hz, 1H), 7.28 (dd, J=3.6, 5.1 Hz, 1H), 7.16 (d, J=3.6 Hz, 1H), 7.01 (brs, 2H), 5.64 (brs, 2H), 4.84 (brs, 1H), 3.16 (s, 2H), 2.94 (m, 2H), 1.86 (m, 2H). ES MS m/z 331 (M+H)+, 329 (M−H)−.

Workup

  1. additionwas added dropwise
  2. customevaporated to dryness under vacuum
  3. customThe residue was purified by silica gel column (chloroform/methanol, 30:1)
  4. customto give a yellow solid

Sources & evidence

ORD record
ord-b777b558217c43dfa2c70f9edf54497f
Source dataset
uspto-grants-2008_12
Patent number
US07465742B2

Reaction notes

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