1,2-Dichloroethane → 3-(4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate

HRID 2098379Notes

Reaction equation

HRID 2098379 reaction equation
CN(C)C(OC1C=C([NH:12][C:13]([C:15]2(C)[CH2:20][CH2:19][N:18]([C:21](OC(C)(C)C)=O)C[CH2:16]2)=O)C=CC=1)=O.C(O[C:35]([N:37]1[CH2:42][CH2:41][C:40]([CH3:46])([C:43]([OH:45])=O)[CH2:39][CH2:38]1)=O)(C)(C)C.C(Cl)CCl.C1C=CC2N(O)N=[N:57]C=2C=1.ClC(Cl)C.[CH3:65][N:66]([CH3:77])[C:67](=[O:76])[O:68][C:69]1[CH:74]=[CH:73][CH:72]=[C:71]([NH2:75])[CH:70]=1>>[CH3:65][N:66]([CH3:77])[C:67](=[O:76])[O:68][C:69]1[CH:74]=[CH:73][CH:72]=[C:71]([NH:75][C:43]([C:40]2([CH3:46])[CH2:39][CH2:38][N:37]([C:35]3[C:20]4[C:15]([CH3:16])=[CH:13][NH:12][C:19]=4[N:18]=[CH:21][N:57]=3)[CH2:42][CH2:41]2)=[O:45])[CH:70]=1

Participants

7

Reactant 6

HCID 111,2-DichloroethaneHCID 63651,1-DichloroethaneHCID 298773-Aminophenyl dimethylcarbamateHCID 757711-HydroxybenzotriazoleHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acidHCID 67037209Tert-butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-methylpiperidine-1-carboxylate

Product 1

HCID 579201983-(4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamateYield 50%

Conditions

Temperature
85 °C

Procedure

Preparation of tert-butyl 4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-4-methylpiperidine-1-carboxylate. 1-(tert-Butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (67 mg, 0.28 mmol), EDC (64 mg, 0.33 mmol), HOBT (45 mg, 0.33 mmol) and dichloroethane (2.0 mL) were combined in a pressure rated sealed tube and stirred for 45 min. 3-Aminophenyl dimethylcarbamate (50 mg, 0.28 mmol) was added, and the mixture was heated at 85° C. for 18 hours. The mixture was concentrated and chromatographed (SiO2, 0-2% MeOH:CH2Cl2) to give the title compound in 50% yield. MS (ES+) [M+H]+=406.

Workup

  1. customrated sealed tube
  2. concentrationThe mixture was concentrated
  3. customchromatographed (SiO2, 0-2% MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-fb1b83c12b424855b22a699f13e28424
Source dataset
uspto-grants-2013_05
Patent number
US08450332B2

Reaction notes

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