4,5,6,7-Tetrahydro-1,2-benzoxazole-3-carboxylic acid → HCID 70656498, compound

HRID 872900Notes

Reaction equation

HRID 872900 reaction equation
[NH2:1][C@@H:2]([CH3:18])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([Cl:17])[CH:10]=2)=[N:5]1.[O:19]1[C:23]2[CH2:24][CH2:25][CH2:26][CH2:27][C:22]=2[C:21]([C:28](O)=[O:29])=[N:20]1>>[Cl:17][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][N:4]([CH2:3][C@@H:2]([NH:1][C:28]([C:21]3[C:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=4[O:19][N:20]=3)=[O:29])[CH3:18])[N:5]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

3

Reactant 2

HCID 8205614,5,6,7-Tetrahydro-1,2-benzoxazole-3-carboxylic acidHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70656498HCID 70656498, compound

Procedure

The title compound was prepared using the method of Example 34(d) starting from (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (90 mg, 0.345 mmol) and 4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxylic acid (75 mg, 0.449 mmol). The product was purified with flash chromatography. Yield 111 mg (78%). 1H-NMR (400 MHz; CDCl3): δ 1.24 (d, 3H), 1.69-1.83 (m, 4H), 2.77-2.83 (m, 4H), 4.25-4.43 (m, 2H), 4.52-4.61 (m, 1H), 6.63 (d, 1H), 7.37 (d, 1H), 7.49 (d, 1H), 7.70 (d, 1H), 7.86 (d, 1H), 7.94 (d, 1H).

Workup

  1. customThe product was purified with flash chromatography

Sources & evidence

ORD record
ord-58eb2326fa344a1eaf6b107e8cc0bbeb
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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