Diisopropylethylamine → HCID 86694753, compound

HRID 475283Notes

Reaction equation

HRID 475283 reaction equation
[F:1][C:2]1[C:7]2[N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([CH2:17][NH2:18])[CH:3]=1.Cl[C:20]1[N:25]=[C:24]([NH:26][C:27]2[NH:31][N:30]=[C:29]([CH:32]3[CH2:34][CH2:33]3)[CH:28]=2)[CH:23]=[CH:22][N:21]=1.CCN(C(C)C)C(C)C>CC(O)C>[CH:32]1([C:29]2[NH:30][N:31]=[C:27]([NH:26][C:24]3[CH:23]=[CH:22][N:21]=[C:20]([NH:18][CH2:17][C:4]4[CH:3]=[C:2]([F:1])[C:7]5[N:8]([CH:11]6[CH2:16][CH2:15][CH2:14][CH2:13][O:12]6)[CH:9]=[N:10][C:6]=5[CH:5]=4)[N:25]=3)[CH:28]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 86694754HCID 86694754, compoundHCID 178478345HCID 178478345, compound

Product 1

HCID 86694753HCID 86694753, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

A tube was charged with 270 (260 mg, 1.04 mmol), 53 (100 mg, 0.57 mmol), DIPEA (0.5 ml) in IPA (3 mL), degassed, sealed and heated at 120° C. overnight. The solvent was evaporated under reduced pressure to afford 160 mg (34%) N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((7-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methyl)pyrimidine-2,4-diamine (272) as yellow solid: MS (ESI) m/z=449.2 [M+1]+.

Workup

  1. customdegassed
  2. customsealed
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9a0abb7739cc4c13a7e64359fbd6968c
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

Loading…