Diisopropylethylamine → HCID 59199979, compound

HRID 2382106Notes

Reaction equation

[CH3:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([NH2:11])[CH:3]=1.[CH3:12][C:13]1[C:18]([C:19](O)=[O:20])=[CH:17][N:16]=[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:14]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH3:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([NH:11][C:19]([C:18]2[C:13]([CH3:12])=[N:14][C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:16][CH:17]=2)=[O:20])[CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 3-methyl-pyrrolo[3,2-c]pyridin-1-yl amine (223 mg, 1.52 mmol), 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (329 mg, 1.52 mmol), HATU (693 mg, 1.82 mmol) and DIPEA (593 mg, 4.59 mmol) in DMF (8 mL) is stirred at 150° C. for 1 h. The reaction is quenched with water and NaHCO3 (168 mg, 2 mmol). The mixture is concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10% meOH in DCM to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide (91 mg, 17%). MS: 345 (M+H); 1H NMR (300 MHz, DMSO-d6): δ=9.34 (s, 2H), 8.79 (d, 1H), 8.53 (d, 1H), 8.45 (d, 1H), 8.13 (d, 1H), 8.02 (t, 1H), 7.86 (s, 1H), 7.59 (t, 1H), 2.77 (s, 3H), 2.43 (s, 3H).

Workup

concentrationThe mixture is concentrated in vacuo
customThe residue is purified by silica gel chromatography
washeluting with 10% meOH in DCM

Sources & evidence

ORD record: ord-b20b7f893ad64bb18f8dad39ae733102
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258130B2

Reaction notes

Loading…