HCID 19370602, compound → HCID 178432584, compound

HRID 872575Notes

Reaction equation

HRID 872575 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:11]=[C:10]([C:12]([OH:14])=O)[NH:9][N:8]=2)[N:6]=1.[NH2:15][C@@H:16]([CH3:32])[CH2:17][N:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([Cl:31])[CH:24]=2)=[N:19]1>>[Cl:31][C:25]1[CH:24]=[C:23]([C:20]2[CH:21]=[CH:22][N:18]([CH2:17][C@@H:16]([NH:15][C:12]([C:10]3[CH:11]=[C:7]([C:5]4[N:6]=[C:2]([CH3:1])[S:3][CH:4]=4)[NH:8][N:9]=3)=[O:14])[CH3:32])[N:19]=2)[CH:30]=[CH:29][C:26]=1[C:27]#[N:28]

Participants

3

Reactant 2

HCID 19370602HCID 19370602, compoundHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 178432584HCID 178432584, compoundYield 18%

Procedure

3-(2-Methylthiazol-4-yl)-1H-pyrazole-5-carboxylic acid (0.586 mmol) was coupled with (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile using the method of Example 34(d). Crude product was purified by CombiFlash (silica column, eluent: 50-100% EtOAc in heptane) to obtain 24 mg (18%) of the title compound 1H-NMR (400 MHz; CDCl3): δ 1.24 (d, 3H), 2.77 (s, 3H), 4.28 (dd, 1H), 4.44 (dd, 1H), 4.55-4.67 (m, 1H), 6.59 (d, 1H), 7.06 (s, 1H), 7.38 (s, 1H), 7.49 (d, 1H), 7.60 (d, 1H), 7.74 (dd, 1H), 7.82 (d, 1H), 8.06 (d, 1H), 11.75 (bs, 1H).

Workup

  1. customCrude product was purified by CombiFlash (silica column, eluent: 50-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-2b44eeda0cad483ab3373b52543fb2f7
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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