Diisopropylethylamine → HCID 178505998, compound

HRID 475285Notes

Reaction equation

HRID 475285 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([CH2:16][NH2:17])[C:10]=2[N:9]=[CH:8]1.Cl[C:19]1[N:24]=[C:23]([NH:25][C:26]2[CH:30]=[C:29]([CH:31]3[CH2:33][CH2:32]3)[NH:28][N:27]=2)[C:22]([F:34])=[CH:21][N:20]=1.CCN(C(C)C)C(C)C>CC(O)C>[CH:31]1([C:29]2[CH:30]=[C:26]([NH:25][C:23]3[C:22]([F:34])=[CH:21][N:20]=[C:19]([NH:17][CH2:16][C:15]4[C:10]5[N:9]=[CH:8][N:7]([CH:2]6[CH2:3][CH2:4][CH2:5][CH2:6][O:1]6)[C:11]=5[CH:12]=[CH:13][CH:14]=4)[N:24]=3)[NH:27][N:28]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 581693062-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)-5-fluoropyrimidin-4-amineHCID 71272654(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)methanamine

Product 1

HCID 178505998HCID 178505998, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

A tube was charged with 58 (273 mg, 1.18 mmol), 55 (150 mg, 0.59 mmol), DIPEA (0.5 ml) and IPA (4 mL), degassed, sealed and heated at 120° C. for 72 h. The solvent was evaporated in vacuo to afford 150 mg (57%) of N4-(3-cyclopropyl-1H-pyrazol-5-yl)-5-fluoro-N2-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)methyl)pyrimidine-2,4-diamine (280)—as yellow solid: MS (ESI) m/z=449.7 [M+1]+.

Workup

  1. customdegassed
  2. customsealed
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-529d1c31229b4f4f8d2942bdac9b4739
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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