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

HRID 1429747Notes

Reaction equation

HRID 1429747 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-f18bf3bcbec644558bc36d6486be00b6
Source dataset
uspto-grants-2015_01
Patent number
US08940744B2

Reaction notes

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