Ethyl 2-aminothiazole-4-carboxylate → HCID 58869829, compound

HRID 2402293Notes

Reaction equation

HRID 2402293 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[C:4](=[O:35])[N:5]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)[CH:6]2[CH2:12][CH2:13][C:14]([NH:16][C:17]1C=CC(C(F)(F)F)=C[N:18]=1)=[O:15].NC1[S:38][CH:39]=[C:40]([C:42]([O:44][CH2:45][CH3:46])=[O:43])N=1>>[CH2:45]([O:44][C:42]([C:40]1[N:18]=[C:17]([NH:16][C:14](=[O:15])[CH2:13][CH2:12][CH:6]2[C:7]3[C:3](=[C:2]([F:1])[CH:10]=[CH:9][C:8]=3[F:11])[C:4](=[O:35])[N:5]2[CH2:27][C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[S:38][CH:39]=1)=[O:43])[CH3:46]

Participants

3

Reactant 2

HCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 58869805HCID 58869805, compound

Product 1

HCID 58869829HCID 58869829, compound

Procedure

The product from Example 18, Part A (100 mg, 0.29 mmol) and ethyl 2-amino-1,3-thiazole-4-carboxylate were converted to the title compound in a manner analogous to the method described in Example 7, Part E without crystallization (80 mg, 55%). 1H (300 MHz, CDCl3) δ 10.31 (s, 1H), 7.77 (s, 1H), 7.28 (m, 2H), 7.12 (m, 1H), 6.99 (m, 3H), 5.21 (d, J=15 Hz, 1H), 4.65 (m, 1H), 4.32 (q, J=7 Hz, 2H), 4.12 (d, J=15 Hz, 1H), 2.57 (m, 2H), 2.14 (m, 1H), 2.08 (m, 1H), 1.35 (t, J=7 Hz, 3H). MS: m/z (MH+) 504.

Sources & evidence

ORD record
ord-1547eaf4f849497b99fe07ccbf12178e
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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