Diisopropylethylamine → HCID 86694726, compound

HRID 475214Notes

Reaction equation

HRID 475214 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:13][N:12]=[C:11]([CH:14]3[CH2:16][CH2:15]3)[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F:17][C:18]1[C:19]([CH2:33][NH2:34])=[CH:20][C:21]2[N:25]=[CH:24][N:23]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C:22]=2[CH:32]=1.CCN(C(C)C)C(C)C>CC(O)C>[CH:14]1([C:11]2[NH:12][N:13]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:34][CH2:33][C:19]4[C:18]([F:17])=[CH:32][C:22]5[N:23]([CH:26]6[CH2:31][CH2:30][CH2:29][CH2:28][O:27]6)[CH:24]=[N:25][C:21]=5[CH:20]=4)[N:7]=3)[CH:10]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 71272688HCID 71272688, compoundHCID 178478345HCID 178478345, compound

Product 1

HCID 86694726HCID 86694726, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

A tube was charged with 53 (235 mg, 1.0 mmol), 106 (237 mg, 0.95 mmol), DIPEA (1.0 mL) and IPA (3 mL), degassed, sealed and heated at 120° C. overnight. The solvent was evaporated in vacuo to afford 170 mg (39%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((6-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methyl)pyrimidine-2,4-diamine (108) as white solid: MS (ESI) m/z=449.2 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-1e22426538814805a64af21a4f4e34f8
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

Loading…