5-Indanyl isocyanate → (S)-Methyl 2-(5-(4-(3-(2,3-dihydro-1H-inden-5-yl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

HRID 1024467Notes

Reaction equation

HRID 1024467 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH2:8][CH2:7]2)=[C:2]=[O:3].[CH3:13][CH:14]([CH3:37])[CH:15]([NH:20][C:21]([C:23]1[S:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=2)=[CH:26][N:27]=1)=[O:22])[C:16]([O:18][CH3:19])=[O:17]>>[CH2:9]1[C:10]2[C:6](=[CH:5][C:4]([NH:1][C:2](=[O:3])[NH:34][C:31]3[CH:32]=[CH:33][C:28]([C:25]4[S:24][C:23]([C:21]([NH:20][C@@H:15]([CH:14]([CH3:37])[CH3:13])[C:16]([O:18][CH3:19])=[O:17])=[O:22])=[N:27][CH:26]=4)=[CH:29][CH:30]=3)=[CH:12][CH:11]=2)[CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 50036815-Indanyl isocyanateHCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52932945(S)-Methyl 2-(5-(4-(3-(2,3-dihydro-1H-inden-5-yl)ureido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

Procedure

The title compound was synthesized analogous to Example 9, using 5-isocyanato-2,3-dihydro-1H-indene (0.599 mmol) and intermediate 2. 1HNMR (DMSO-d6, 300 MHz): δ ppm 8.891 (s, 1H), 8.732-8.704 (d, 1H), 8.602 (s, 1H), 8.347 (s, 1H), 7.717-7.689 (d, J=8.4 Hz, 2H), 7.575-7.547 (d, J=8.4 Hz, 2H), 7.289 (s, 1H), 7.172-7.101 (m, 2H), 4.349-4.299 (t, J=7.2, 7.8 Hz, 1H), 3.681 (s, 3H), 2.859-2.770 (m, 4H), 2.328-2.204 (m, 1H), 2.054-1.952 (m, 2H), 0.965-0.923 (d, J=6.3 Hz, 6H); MS (ESI) m/z 491 (M−H), 493 (M+H)+.

Sources & evidence

ORD record
ord-7c8a98e43ea24b0d91ca89e1f7e007c0
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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