2,6-Difluorophenyl isocyanate → HCID 67219716, compound

HRID 916760Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]=[C:10]=[O:11].[NH2:12][C:13]1[C:14]2[C:21]([C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=3)=[O:23])=[CH:20][N:19]([CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[C:15]=2[N:16]=[CH:17][N:18]=1>N1C=CC=CC=1>[NH2:12][C:13]1[C:14]2[C:21]([C:22]([C:24]3[CH:25]=[C:26]([NH:30][C:10]([NH:9][C:3]4[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=4[F:8])=[O:11])[CH:27]=[CH:28][CH:29]=3)=[O:23])=[CH:20][N:19]([CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)[C:15]=2[N:16]=[CH:17][N:18]=1

Participants

Conditions

Temperature: 90 °C

Procedure

2,6-Difluorophenyl isocyanate (36.1 mg, 0.233 mmol) was added to a solution of (4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)-methanone (50 mg, 0.15 mol) in pyridine (3 mL). The resulting solution was heated to 90° C. for 3 h. The reaction was quenched with water and concentrated. The residue was dissolved in EtOAc and washed with water. The organic layer was dried over Na2SO4 and concentrated. Purification by flash column chromatography (CH2Cl2/MeOH 98:2) afforded the title compound as a yellow solid (21 mg, 28%). MS: 477.2/322.2 (MH+); HPLC Rf: 5.66 min. (HPLC method

Workup

customThe reaction was quenched with water
concentrationconcentrated
dissolutionThe residue was dissolved in EtOAc
washwashed with water
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated
customPurification by flash column chromatography (CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record: ord-49dd570f83324f2e9c1dc11562476740
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271262B2

Reaction notes

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