2-Aminothiazole → HCID 23624259, compound

HRID 1677670Notes

Reaction equation

HRID 1677670 reaction equation
[N:1]1[N:2]([CH:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:13])=O)[CH:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2.[NH2:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CCN(CC)CC>CN(C=O)C>[N:1]1[N:2]([CH:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([NH:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[O:13])[CH:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58506951HCID 58506951, compound

Product 1

HCID 23624259HCID 23624259, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Compound 1 (640 mg, 2.76 mmol), 2-aminothiazole (284 mg, 2.76 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) (1.0 g, 2.76 mmol) and 0.2 mL of Et3N in DMF (4 mL) was stirred at room temperature for 2 hours to provide the title compound, which was then purified by HPLC. 1H NMR (400 MHz, DMSO-d6) δ: 7.74 (d, J=12.0 Hz, 1H), 7.60 (d, J=12.0 Hz, 1H), 7.51 (d, J=4.0 Hz, 1H), 7.25 (m, 2H), 7.05 (t, J=8.0, 8.0 Hz, 1H), 5.67 (m, 1H), 2.23 (m, 1H), 2.06 (m, 1H), 1.32 (m, 1H), 0.94 (d, J=8.0 Hz, 3H), 0.90 (d, J=8.0 Hz, 3H). [M+H] calc'd for C16H18OS, 314. found, 314.

Sources & evidence

ORD record
ord-b35b273ca2f94f6588ad82a0054e3b7b
Source dataset
uspto-grants-2011_08
Patent number
US08008332B2

Reaction notes

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