2-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide → HCID 66829506, compound

HRID 1040617Notes

Reaction equation

HRID 1040617 reaction equation
C(OC([N:8]1[CH2:18][CH:17]2[O:19][CH:10]([C:11]3[C:16]2=[CH:15][C:14]([NH2:20])=[CH:13][CH:12]=3)[CH2:9]1)=O)(C)(C)C.Cl[C:22]1[N:27]=[C:26]([NH:28][C:29]2[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=2[C:31]([NH:33][CH3:34])=[O:32])[C:25]([Cl:39])=[CH:24][N:23]=1>COCCO.C([O-])(O)=O.[Na+]>[Cl:39][C:25]1[C:26]([NH:28][C:29]2[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=2[C:31]([NH:33][CH3:34])=[O:32])=[N:27][C:22]([NH:20][C:14]2[CH:13]=[CH:12][C:11]3[CH:10]4[O:19][CH:17]([CH2:18][NH:8][CH2:9]4)[C:16]=3[CH:15]=2)=[N:23][CH:24]=1

Participants

5

Reactant 2

HCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideHCID 67264262HCID 67264262, compound

Product 1

HCID 66829506HCID 66829506, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

4-Amino-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene-10-carboxylic acid tert-butyl ester (220 mg, 0.80 mmol) and 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide (236 mg, 0.80 mmol) were combined in 2-methoxyethanol (3 mL) and heated at 120° C. for 6 h. The reaction was then was diluted with saturated aqueous NaHCO3 (3 mL), extracted with CH2Cl2 (3×5 mL), dried over MgSO4, filtered, and concentrated. The resulting residue was purified with silica gel chromatography (0-30% MeOH in EtOAc) to obtain 2-[5-Chloro-2-(12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide as a tan solid (34 mg, 10%). 1HNMR (400 MHz, CDCl3) δ 11.0 (bs, 1H), 8.6 (d, 1H, J=8.3 Hz), 8.0 (s, 1H), 7.6 (s, 1H), 7.5 (d, 1H, J=7.8 Hz), 7.4 (m, 2H), 7.3 (d, 1H, J=7.8 Hz), 7.1 (d, 1H, J=8.1 Hz), 7.0 (appt t, 1H, J=7.6 Hz), 6.5 (bs, 1H), 5.0 (s, 1H), 4.9 (s, 1H), 3.3 (t, 2H, J=13.5 Hz), 3.0 (d, 3H, J=4.8 Hz), 2.9 (bs, 1H), 2.6 (t, 2H, J=13.5 Hz); MS (m/e) 437 (M+1); mp 164-168° C.

Workup

  1. extractionextracted with CH2Cl2 (3×5 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified with silica gel chromatography (0-30% MeOH in EtOAc)

Sources & evidence

ORD record
ord-9f4cc358c5d745228ad9c76e488cd093
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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