Phenyl (5-acetyl-4-methyl-1,3-thiazol-2-yl)carbamate → HCID 10195948, compound

HRID 2108350Notes

Reaction equation

HRID 2108350 reaction equation
C(O[C:9](=[O:33])[NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:17][N:18]1[CH2:23][C:22](=[O:24])[NH:21][C@@H:20]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:19]1)C1C=CC=CC=1.C1(OC(=O)[NH:42][C:43]2[S:44][C:45]([C:49](=[O:51])[CH3:50])=[C:46]([CH3:48])[N:47]=2)C=CC=CC=1>C(C#N)(C)=O>[C:49]([C:45]1[S:44][C:43]([NH:42][C:9]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[CH2:17][N:18]2[CH2:23][C:22](=[O:24])[NH:21][C@@H:20]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:19]2)=[O:33])=[N:47][C:46]=1[CH3:48])(=[O:51])[CH3:50]

Participants

4

Reactant 2

HCID 22259036Phenyl (5-acetyl-4-methyl-1,3-thiazol-2-yl)carbamateHCID 68824588HCID 68824588, compound

Product 1

HCID 10195948HCID 10195948, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Procedure

A solution of amine from EXAMPLE 3 (75 mg, 0.23 mmol) and carbamate from EXAMPLE 6 (65 mg, 0.23 mmol) in AcCN (4 ml) was warm to 45° C. for 30 minutes. A solid form and the mixture cooled to room temperature and the solid filtered off to give 50 mg of the desired urea. 1H NMR (300 MHz, CDCl3) δ12.21 (bs, 1H), 8.56 (bs, 1H), 6.99-6.90 (m, 4H), 5.49 (bd, J=8 Hz, 1H), 3.52 (m, 1H), 3.40 (m, 1H), 3.24 (d, J=17 Hz, 1H), 2.96 (d, J=17 Hz, 1H), 2.88 (dd, J=5 Hz, J=14 Hz, 1H), 2.73 (dd, J=9 Hz, J=14 Hz, 1H), 2.54 (m, 2H), 2.47 (s, 6H), 2.20-2.06 (m, 3H), 1.90-1.76 (m, 4H), 1.43-1.00 (m, 4H). ESI MS: (M+H)+=502.2; HRMS: (M+H)+=502.2287.

Workup

  1. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-5b6b53c0d57e49ffb6f849502cc481bd
Source dataset
uspto-grants-2009_04
Patent number
US07514430B2

Reaction notes

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