(S)-pyrrolidine-2-carbonyl chloride hydrochloride → (S)-(4-(4-(5-chloro-4-(2-(isopropylsulfonyl)phenylamino)pyrimidin-2-ylamino)-5-isopropoxy-2-methylphenyl)piperidin-1-yl)(pyrrolidin-2-yl)methanone

HRID 2046959Notes

Reaction equation

HRID 2046959 reaction equation
[Cl:1][C:2]1[C:3]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[S:33]([CH:36]([CH3:38])[CH3:37])(=[O:35])=[O:34])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:11][C:10]=2[O:22][CH:23]([CH3:25])[CH3:24])=[N:6][CH:7]=1.Cl.[NH:40]1[CH2:44][CH2:43][CH2:42][C@H:41]1[C:45](Cl)=[O:46]>>[Cl:1][C:2]1[C:3]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[S:33]([CH:36]([CH3:38])[CH3:37])(=[O:35])=[O:34])=[N:4][C:5]([NH:8][C:9]2[C:10]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:11][C:12]([CH:16]3[CH2:21][CH2:20][N:19]([C:45]([C@@H:41]4[CH2:42][CH2:43][CH2:44][NH:40]4)=[O:46])[CH2:18][CH2:17]3)=[C:13]([CH3:15])[CH:14]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 12378857(S)-pyrrolidine-2-carbonyl chloride hydrochlorideHCID 57379345Ceritinib

Product 1

HCID 44467546(S)-(4-(4-(5-chloro-4-(2-(isopropylsulfonyl)phenylamino)pyrimidin-2-ylamino)-5-isopropoxy-2-methylphenyl)piperidin-1-yl)(pyrrolidin-2-yl)methanone

Procedure

Prepared according to the method of Example 1 by replacing N6-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine with 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine and replacing 2-(dimethylamino)acetyl chloride hydrochloride with (S)-pyrrolidine-2-carbonyl chloride hydrochloride. Product was obtained. MS (ES+): 655.28 (M+1).

Workup

  1. customPrepared
  2. customProduct was obtained

Sources & evidence

ORD record
ord-a5bba41d027049728252108e6576f859
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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