Ammonia → HCID 11993590, compound

HRID 1364497Notes

Reaction equation

HRID 1364497 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].N.CO.CC[N:25](C(C)C)C(C)C>C(Cl)Cl>[NH2:25][S:16]([C:14]1[S:15][C:11]([C:7]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=2[CH3:10])=[CH:12][CH:13]=1)(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 81531DiisopropylethylamineHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11993590HCID 11993590, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step 1 of Example 9 (200 mg; 0.59 mmol; 1 eq.), is dissolved in DCM (10 ml). A solution of ammonia in MeOH (0.59 ml; 2 M; 1.19 mmol; 2 eq.) and DIEA (460.4 mg; 3.56 mmol; 6 eq.) are added. After one hour, the solvents are evaporated. The crude product is purified by preparative HPLC, affording Compound (17) as white-off solid (36 mg; 17%). 1H NMR (DMSO-d6) δ 2.14 (s, 3H), 2.42 (s, 3H), 7.16 (d, J=4.5 Hz, 1H), 7.50 (d, J=4.5 Hz, 1H), 7.72 (s, 2H), 12.30 (s, 1H). M−(ESI): 316.07; M+(ESI): 318.10. HPLC, Rt: 2.16 min (purity: 99.8%).

Workup

  1. customthe solvents are evaporated
  2. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-76aa02ee44a84578bb5c10f781779818
Source dataset
uspto-grants-2011_02
Patent number
US07888379B2

Reaction notes

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