HCID 178421711, compound → HCID 86617879, compound

HRID 2426812Notes

Reaction equation

HRID 2426812 reaction equation
[CH2:1]([N:8]([CH2:46][CH:47]1[CH2:49][CH:48]1[CH3:50])[C:9]1[CH:14]=[C:13]([C:15]2[N:20]=[CH:19][NH:18][CH:17]([C@@:21]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:29])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:16]=2)[CH:12]=[C:11]([N:38]([S:40]([CH:43]([CH3:45])[CH3:44])(=[O:42])=[O:41])[CH3:39])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH2:1]([N:8]([CH2:46][CH:47]1[CH2:49][CH:48]1[CH3:50])[C:9]1[CH:14]=[C:13]([C:15]2[N:20]=[CH:19][N:18]=[C:17]([C@@:21]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])([CH3:29])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:16]=2)[CH:12]=[C:11]([N:38]([S:40]([CH:43]([CH3:44])[CH3:45])(=[O:42])=[O:41])[CH3:39])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 178421711HCID 178421711, compound

Product 1

HCID 86617879HCID 86617879, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl (1R)-1-(6-{2-{benzyl[(2-methylcyclopropyl)methyl]amino}-6-[(isopropylsulfonyl)(methyl)amino]pyridin-4-yl}-3,4-dihydropyrimidin-4-yl)-1-methyl-2-phenylethylcarbamate from Step A above (49 mg, 0.07 mmol) in 2 mL toluene was added dichlorodicyanoquinone (24 mg, 0.11 mmol). The resulting solution was heated at 120 degrees for 30 min., then cooled to it and concentrated to dryness. Purification by reverse phase chromatography yielded tert-butyl (1R)-1-(6-{2-{benzyl[(2-methylcyclopropyl)methyl]amino}-6-[(isopropylsulfonyl)(methyl)amino]pyridin-4-yl}pyrimidin-4-yl)-1-methyl-2-phenylethylcarbamate, which was taken up in 1 mL 20% TFA in dichloromethane. The mixture was allowed to sit for 1 hour, and was concentrated to afford the title compound N-(4-{6-[(1R)-1-amino-1-methyl-2-phenylethyl]pyrimidin-4-yl}-6-{benzyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylpropane-2-sulfonamide. 1H NMR (400 MHz, d4-MeOH) δ 9.29 (s, 1H), 7.66-7.65 (m, 1H), 7.31-7.21 (m, 8H), 7.02-7.01 (m, 2H), 6.96-6.93 (m, 2H), 4.98-4.60 (m, 2H), 3.83-3.66 (m, 2H), 3.38 (s, 3H), 3.35-3.25 (m, 4H), 1.81 (s, 3H), 1.16 (d, J=6.8 Hz), 0.96 (dd, J=6 Hz, J=1.8 Hz, 3H) 0.90-0.82 (m, 1H), 0.70-0.62 (m, 1H), 0.45-0.40 (m, 1H), 0.28-0.24 (m, 1H); LCMS [M+H]=599.1.

Workup

  1. temperatureThe resulting solution was heated at 120 degrees for 30 min.
  2. temperaturecooled to it
  3. concentrationconcentrated to dryness
  4. customPurification by reverse phase chromatography

Sources & evidence

ORD record
ord-dd99f631b1a646ec980d4605f99b8ce9
Source dataset
uspto-grants-2011_06
Patent number
US07968571B2

Reaction notes

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