Allylamine → HCID 11961259, compound

HRID 1364492Notes

Reaction equation

HRID 1364492 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].[CH2:20]([NH2:23])[CH:21]=[CH2:22].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:20]([NH:23][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])[CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 81531DiisopropylethylamineHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11961259HCID 11961259, 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 (110 mg; 0.33 mmol; 1 eq.), is dissolved in DCM (10 ml). Allylamine (0.034 ml; 0.46 mmol; 1.40 eq.) and DIEA (0.17 ml; 0.98 mmol; 3 eq.) are added. After one hour, the solvents are evaporated. The crude product is purified by preparative HPLC, affording Compound (12) is obtained as white-off solid (75 mg; 50%). 1H NMR (DMSO-d6) δ 2.22 (s, 3H), 2.51 (s, 3H), 3.61 (m, 2H), 5.14 (m, 1H), 5.26 (m, 1H), 5.80 (m, 1H), 7.28 (d, J=3.8 Hz, 1H), 7.62 (d, J=3.8 Hz, 1H), 8.17 (t, J=6 Hz, 1H), 12.39 (s, 1H). M−(ESI): 356.12; M+(ESI): 358.12. HPLC, Rt: 3.06 min (purity: 100%).

Workup

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

Sources & evidence

ORD record
ord-df12f8d50bad47728913a64e4de0a103
Source dataset
uspto-grants-2011_02
Patent number
US07888379B2

Reaction notes

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