Triethylamine → 2-Fluoroethyl{4-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1h-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}carbamate

HRID 1093300Notes

Reaction equation

HRID 1093300 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([C:15]3[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=3)[N:12]=[C:11]3[N:22]([CH:25]4[CH2:34][CH2:33][C:28]5([O:32][CH2:31][CH2:30][O:29]5)[CH2:27][CH2:26]4)[N:23]=[CH:24][C:10]=13)[CH2:2]2.C(N(CC)CC)C.Cl[C:43]([O:45][CH2:46][CH2:47][F:48])=[O:44]>ClCCl>[F:48][CH2:47][CH2:46][O:45][C:43](=[O:44])[NH:19][C:18]1[CH:20]=[CH:21][C:15]([C:13]2[N:12]=[C:11]3[N:22]([CH:25]4[CH2:34][CH2:33][C:28]5([O:29][CH2:30][CH2:31][O:32]5)[CH2:27][CH2:26]4)[N:23]=[CH:24][C:10]3=[C:9]([N:3]3[CH2:4][CH:5]4[O:8][CH:1]([CH2:7][CH2:6]4)[CH2:2]3)[N:14]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10017Carbonochloridic acid, 2-fluoroethyl esterHCID 252621774-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline

Product 1

HCID 913402332-Fluoroethyl{4-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1h-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

was also prepared by an alternative route: 36 mg 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline was dissolved in dichloromethane (0.5 mL) containing triethylamine (100 uL). 93 uL 2-fluoroethyl chloroformate was added and the mixture was stirred for 30 minutes. The mixture was concentrated and the title compound was obtained after HPLC purification. MS: 553.2 [M+H], RT 2.42.

Workup

  1. customwas also prepared by an alternative route
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-7a462d8aa3794b9e84a9ad72eb0a89e2
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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