2-Amino-5-cyanopyridine → (S)-3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-N-(5-cyanopyridin-2-yl)-2-(1-(2,6-dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide

HRID 1098271Notes

Reaction equation

HRID 1098271 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[Si:10]([O:17][CH:18]1[CH2:21][N:20]([CH2:22][C@H:23]([O:28][C:29]2[N:34]=[CH:33][N:32]=[C:31]3[N:35]([C:38]4[C:43]([Cl:44])=[CH:42][CH:41]=[CH:40][C:39]=4[Cl:45])[N:36]=[CH:37][C:30]=23)[C:24](OC)=[O:25])[CH2:19]1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>>[Si:10]([O:17][CH:18]1[CH2:19][N:20]([CH2:22][C@H:23]([O:28][C:29]2[N:34]=[CH:33][N:32]=[C:31]3[N:35]([C:38]4[C:39]([Cl:45])=[CH:40][CH:41]=[CH:42][C:43]=4[Cl:44])[N:36]=[CH:37][C:30]=23)[C:24]([NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=2)=[O:25])[CH2:21]1)([C:13]([CH3:15])([CH3:16])[CH3:14])([CH3:11])[CH3:12]

Participants

3

Reactant 2

HCID 8182602-Amino-5-cyanopyridineHCID 66813287(S)-methyl 3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-2-(1-(2,6-dichlorophenyl)-1H-pyrazolo [3,4-d]pyrimidin-4-yloxy)propanoate

Product 1

HCID 57504719(S)-3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-N-(5-cyanopyridin-2-yl)-2-(1-(2,6-dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide

Procedure

Using a procedure analogous to that described for Intermediate BD12 using 6-aminonicotinonitrile and (S)-methyl 3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-2-(1-(2,6-dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanoate (Intermediate BJ1).

Sources & evidence

ORD record
ord-913325eb378c440eaa7caf7c425bf33b
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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