Diisopropylethylamine → HCID 57496295, compound

HRID 1864142Notes

Reaction equation

HRID 1864142 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([N:13]2[C:17]3=[N:18][CH:19]=[N:20][C:21](Cl)=[C:16]3[CH:15]=[N:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:25]([O:29][C:30](=[O:39])[NH:31][CH:32]1[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34][CH2:33]1)([CH3:28])([CH3:27])[CH3:26].C(N(C(C)C)CC)(C)C>C1COCC1>[C:25]([O:29][C:30](=[O:39])[NH:31][CH:32]1[CH2:33][CH2:34][CH:35]([NH:38][C:21]2[N:20]=[CH:19][N:18]=[C:17]3[N:13]([C:5]4[CH:4]=[C:3]([C:2]([F:24])([F:23])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=4)[N:14]=[CH:15][C:16]=23)[CH2:36][CH2:37]1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamateHCID 21897736HCID 21897736, compound

Product 1

HCID 57496295HCID 57496295, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3,5-Bis-trifluoromethyl-phenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (147 mg, 0.4 mmol), (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (0.44 mmole, 1.1 eq) and diisopropylethyl amine (0.44 mmol, 1.1 eq) were dissolved in THF (3 mL) and then stirred at room temperature over night. THF was removed in vacuo and the solid residue was re-dissolved in 30/70 mixture of water and ACN gave yellow solid. The solid was washed with water and dried in vacuo provided compound A44 as creamy green solid (179 mg, 82%). 1H NMR (CDCl3, 400MHz) δ 1.43 (s, 9H), 1.75 (m, 2H), 1.98-1.97 (m, 2H), 2.04 (m, 2H), 2.95 (sb, 2H), 4.12 (q, 1H), 4.62 (m, 1H), 7.80 (s, 1H), 8.09 (s, 1H), 8.50 (s, 1H), 8.94 (s, 2H). Exact mass calculated for C24H26F6N6O2 544.2, Found 545.5 (MH+).

Workup

  1. customTHF was removed in vacuo
  2. dissolutionthe solid residue was re-dissolved in 30/70 mixture of water and ACN
  3. customgave yellow solid
  4. washThe solid was washed with water
  5. customdried in vacuo
  6. customprovided compound

Sources & evidence

ORD record
ord-791737ff549e4cfa97f3fa39433bea04
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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