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

HRID 1024472Notes

Reaction equation

HRID 1024472 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][CH:25]=[C:26]([C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=2)[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:26]4[N:27]=[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])[S:24][CH:25]=4)=[CH:29][CH:30]=3)=[CH:12][CH:11]=2)[CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 50036815-Indanyl isocyanateHCID 67150325Methyl 3-methyl-2-(4-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52933673(S)-Methyl 2-(4-(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 23, using 2,3-dihydro-5-isocyanato-1H-indene and intermediate 3. 1HNMR (DMSO-d6, 300 MHz): δ 8.817-8.795 (d, 2H), 8.578 (s, 1H), 8.306 (s, 1H), 8.040-8.011 (d, J=8.7 Hz, 2H), 7.582-7.553 (d, J=8.7 Hz, 2H), 7.401 (s, 1H), 7.170-7.104 (m, 2H), 4.394-4.342 (t, J=7.5, 8.1 Hz, 1H), 3.700 (s, 3H), 2.863-2.773 (m, 4H), 2.343-2.274 (m, 1H), 2.087-1.981 (m, 2H), 1.001-0.953 (t, J=7.2 Hz, 6H); MS (ESI) m/z 491 (M−H), 493 (M+H)+.

Sources & evidence

ORD record
ord-939e457c318b497faf5904b0f80a1f91
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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