2-Cyano-4-methylpent-2-enoic acid → HCID 123659276, compound

HRID 1778444Notes

Reaction equation

HRID 1778444 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[C:9]3=[N:10][CH:11]=[N:12][C:13]([NH2:14])=[C:8]3[C:7]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][C:16]=3[F:28])=[N:6]2)[CH2:2]1.[C:29]([C:31](=[CH:35][CH:36]([CH3:38])[CH3:37])[C:32](O)=[O:33])#[N:30].C1CN([P+](ON2N=NC3C=CC=NC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[NH2:14][C:13]1[N:12]=[CH:11][N:10]=[C:9]2[N:5]([CH:3]3[CH2:2][N:1]([C:32]([C:31](=[CH:35][CH:36]([CH3:38])[CH3:37])[C:29]#[N:30])=[O:33])[CH2:4]3)[N:6]=[C:7]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][C:16]=3[F:28])[C:8]=12

Participants

5

Reactant 3

HCID 2925472-Cyano-4-methylpent-2-enoic acidHCID 11038641((7-Azabenzotriazol-1-YL)oxy)tris(pyrrolidino)phosphonium hexafluorophosphateHCID 117728446HCID 117728446, compound

Product 1

HCID 123659276HCID 123659276, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of 1-(azetidin-3-yl)-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-4-amine (80 mg, 0.210 mmol, 2-cyano-4-methyl-pent-2-enoic acid (44.4 mg, 0.320 mmol), PyAOP (121.9 mg, 0.230 mmol) and TEA (0.09 mL, 0.640 mmol) in DCM (3 mL), were stirred overnight at room temperature. The solvent was removed and the residue was purified on a silica gel plate using 6:94 MeOH:CH2Cl2 to get 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]azetidine-1-carbonyl]-4-methyl-pent-2-enenitrile (34 mg) as white powder. LC-MS (ES, m/z): 498 [M+H].

Workup

  1. customThe solvent was removed
  2. customthe residue was purified on a silica gel plate

Sources & evidence

ORD record
ord-54dc436e49b1426483071c264a588766
Source dataset
uspto-grants-2016_02
Patent number
US09266895B2

Reaction notes

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