Methyl chloroformate → HCID 178462816, compound

HRID 1884913Notes

Reaction equation

HRID 1884913 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:17]=[C:16]([NH:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([OH:25])[CH2:21][CH2:20]3)[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH2:26][CH3:27])=[CH:4][CH:3]=1.Cl[C:29]([O:31][CH3:32])=[O:30]>ClCCl>[CH3:32][O:31][C:29](=[O:30])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:17]=[C:16]([NH:18][C@H:19]3[CH2:20][CH2:21][C@H:22]([OH:25])[CH2:23][CH2:24]3)[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH2:26][CH3:27])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6586Methyl chloroformate2×HCID 178462815HCID 178462815, compound

Product 1

HCID 178462816HCID 178462816, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

trans 4-[6-(4-amino-phenylamino)-9-ethyl-9H-purin-2-yl-amino]-cyclohexanol (example 77, stage 1.2, 100 mg, 0.272 mmol) is suspended in 1 ml dichloromethane and treated with 21 μl (0.272 mmol) methyl chloroformate. The reaction mixture is stirred at RT for 20 h after which another equivalent of methyl chloroformate (21 μl, 0.272 mmol) is added. After additional 23 h at RT the reaction mixture is evaporated and the product purified by chromatography on silica gel (CH2Cl2/MeOH 95:5). {4-[9-ethyl-2-(trans-4-hydroxy-cyclo-hexylamino)-9H-purin-6-yl-amino]-phenyl}-carbamic acid methyl ester is obtained as tan crystals, 93 mg (81%). m.p. 131-135° C.; MS [M+H]+426; HPLC (System h) tR=4.84 min.

Workup

  1. additionis added
  2. customAfter additional 23 h at RT the reaction mixture is evaporated
  3. customthe product purified by chromatography on silica gel (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-d9b4407dc54a4353b5fb9997bfed9e98
Source dataset
uspto-grants-2004_07
Patent number
US06767906B2

Reaction notes

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