Diisopropylethylamine → HCID 53482199, compound

HRID 2036581Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[F:20][C:21]1[CH:22]=[CH:23][C:24]2[N:28]=[C:27]([CH:29]([NH2:31])[CH3:30])[N:26]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=3)[C:25]=2[CH:39]=1>C(O)CCC>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:31][CH:29]([C:27]2[N:26]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=3)[C:25]3[CH:39]=[C:21]([F:20])[CH:22]=[CH:23][C:24]=3[N:28]=2)[CH3:30])[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a microwave vessel was added 4-amino-6-chloropyrimidine-5-carbonitrile (B) (0.057 g, 0.366 mmol), DIEA (0.192 mL, 1.098 mmol), and 1-(6-fluoro-1-(3-fluorophenyl)-1H-benzo[d]imidazol-2-yl)ethanamine (0.100 g, 0.366 mmol) in n-butanol (3.66 mL). The solution was stirred at 120° C. under microwave irradiation for 2 h and then purified by column chromatography on a silica gel column using 0 to 10% gradient of MeOH in DCM as eluent to give a racemic mixture 4-amino-6-((1-(6-fluoro-1-(3-fluorophenyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarbonitrile as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54 (d, J=6.65 Hz, 3H) 5.56 (qd, J=6.91, 6.65 Hz, 1H) 6.93 (dd, J=9.00, 2.35 Hz, 1H) 7.08-7.15 (m, 1H) 7.17 (br. s., 2H) 7.31 (td, J=8.41, 2.15 Hz, 1H) 7.35-7.40 (m, 1H) 7.48 (d, J=9.59 Hz, 1H) 7.56 (td, J=8.12, 6.65 Hz, 1H) 7.69 (d, J=7.63 Hz, 1H) 7.73 (dd, J=8.80, 4.89 Hz, 1H) 7.86 (s, 1H); LC-MS (ESI) m/z 392.1 [M+H]+. The racemic mixture (0.085 g) was separated by chiral separation using SFC to give two fractions:

Workup

custompurified by column chromatography on a silica gel column

Sources & evidence

ORD record: ord-af9131f5a5bc4f4ab2898e2409d0c2cf
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575183B2

Reaction notes

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