tert-butyl 9-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-7-chloro-6-cyano-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate → 9-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-7-chloro-2,3,4,5-tetrahydro-1,4-benzoxazepine-6-carbonitrile bishydrochloride

HRID 626843Notes

Reaction equation

HRID 626843 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[C:24]4[O:23][CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C:18]=4[C:17]([C:32]#[N:33])=[C:16]([Cl:34])[CH:15]=3)[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12>Cl.O1CCOCC1>[ClH:34].[ClH:34].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[CH:15]=[C:16]([Cl:34])[C:17]([C:32]#[N:33])=[C:18]4[C:24]=3[O:23][CH2:22][CH2:21][NH:20][CH2:19]4)[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12

Participants

4

Reactant 1

HCID 86697535tert-butyl 9-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-7-chloro-6-cyano-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Product 1

HCID 866975369-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-7-chloro-2,3,4,5-tetrahydro-1,4-benzoxazepine-6-carbonitrile bishydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The crude tert-butyl 9-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-7-chloro-6-cyano-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate was dissolved in 4.0 M hydrogen chloride in dioxane (4.0 mL) at room temperature and was stirred for 1 h. The reaction was concentrated in vacuo to give 9-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-7-chloro-2,3,4,5-tetrahydro-1,4-benzoxazepine-6-carbonitrile bishydrochloride as an off white solid (0.065 g, 66%). LCMS calculated for C18H19ClN7O (M+H)+: m/z=384.1; found: 384.2.

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-77ad394650624d18a9c8e5d8df8dc0c3
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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