Diisopropylethylamine → HCID 86694722, compound

HRID 475190

Reaction equation

HRID 475190 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.CCN(C(C)C)C(C)C.Cl[C:28]1[N:33]=[C:32]([NH:34][C:35]2[NH:39][N:38]=[C:37]([CH:40]3[CH2:42][CH2:41]3)[CH:36]=2)[CH:31]=[CH:30][N:29]=1>CC(O)C>[CH:40]1([C:37]2[NH:38][N:39]=[C:35]([NH:34][C:32]3[CH:31]=[CH:30][N:29]=[C:28]([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:33]=3)[CH:36]=2)[CH2:42][CH2:41]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 71272654(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)methanamineHCID 178478345HCID 178478345, compound

Product 1

HCID 86694722HCID 86694722, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 58 (200 mg, 0.87 mmol), DIPEA (335 mg, 2.61 mmol) and 53 (203 mg, 0.87 mmol) in IPA (3 mL) was irradiated in a microwave reactor at 120° C. for 2 h. The solvent was removed under reduced pressure to afford 110 mg (30%) of crude N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)methyl)pyrimidine-2,4-diamine (60) as brown solid, which was used in the step without further purification: MS (ESI) m/z=431.7 [M+1]+.

Workup

  1. customwas irradiated in a microwave reactor at 120° C. for 2 h
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-29342d3d9b304af39d8faa7ce9a7587e
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Linked notes

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