HCID 58169323, compound → HCID 58169323, compound

HRID 1484917Notes

Reaction equation

HRID 1484917 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([F:16])=[CH:14][N:13]=[C:12]([C:17]4[S:21][C:20]([C@@H:22]([OH:24])[CH3:23])=[CH:19][CH:18]=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[CH:25]1([C:28]2[NH:32][N:31]=[C:30]([NH:33][C:34]3[C:39]([F:40])=[CH:38][N:37]=[C:36]([C:41]4[S:45][C:44]([C@H:46]([OH:48])[CH3:47])=[CH:43][CH:42]=4)[N:35]=3)[CH:29]=2)[CH2:27][CH2:26]1>>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([F:16])=[CH:14][N:13]=[C:12]([C:17]4[S:21][C:20]([C@@H:22]([OH:24])[CH3:23])=[CH:19][CH:18]=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[CH:25]1([C:28]2[NH:32][N:31]=[C:30]([NH:33][C:34]3[C:39]([F:40])=[CH:38][N:37]=[C:36]([C:41]4[S:45][C:44]([C@H:46]([OH:48])[CH3:47])=[CH:43][CH:42]=4)[N:35]=3)[CH:29]=2)[CH2:27][CH2:26]1.[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([F:16])=[CH:14][N:13]=[C:12]([C:17]4[S:21][C:20]([CH:22]([OH:24])[CH3:23])=[CH:19][CH:18]=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 58169323HCID 58169323, compoundHCID 58169431HCID 58169431, compound

Product 3

HCID 58169323HCID 58169323, compoundHCID 58169431HCID 58169431, compoundHCID 58169468HCID 58169468, compound

Procedure

(S)-1-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoropyrimidin-2-yl)thiophen-2yl)ethanol (Compound 144) (80 mg) and (R)-1-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoropyrimidin-2-yl)thiophen-2-yl)ethanol (Compound 147) (75 mg) were obtained by Prep-Chiral-HPLC from the above racemic 1-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoropyrimidin-2-yl)thiophen-2-yl)ethanol (350 mg). The stereostructure of and (R)-1-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoropyrimidin-2-yl)thiophen-2-yl)ethanol (Compound 147) was confirmed by the comparable sample prepared from 1-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoropyrimidin-2-yl)thiophen-2-yl)ethanone with BH3/S-CBS-Me. Synthetic procedures described as following:

Sources & evidence

ORD record
ord-41c815e98cbe4ef49ce3d83057ce3615
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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