4-Aminopyridine → HCID 44512903, compound

HRID 2094574Notes

Reaction equation

HRID 2094574 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[C:13]([O:17][C:18]([N:20]1[CH2:23][CH:22]([CH2:24][NH:25][C:26]2[N:31]=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=3)[N:29]=[C:28]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[N:27]=2)[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[NH2:45][C:46]1[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=1.CCN(CC)CC>C(Cl)Cl>[C:13]([O:17][C:18]([N:20]1[CH2:23][CH:22]([CH2:24][NH:25][C:26]2[N:27]=[C:28]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[N:29]=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([NH:38][C:5]([NH:45][C:46]4[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=4)=[O:11])=[CH:34][CH:33]=3)[N:31]=2)[CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 67021980HCID 67021980, compound

Product 1

HCID 44512903HCID 44512903, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of triphosgene (269 mg, 0.90 mmol) in CH2Cl2 (5 mL) was added 3-{[4-(4-Amino-phenyl)-6-morpholin-4-yl-[1,3,5]triazin-2-ylamino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester (500 mg, 1.13 mmol) at 25° C. The reaction mixture was stirred for 15 min and 4-aminopyridine (319 mg, 3.39 mmol) and NEt3 (1.56 mL, 11.3 mmol) were added and the reaction mixture was stirred for additional 1 hr. The solvents were removed on a rotary evaporator and the crude mixture was purified by semi-prep-HPLC (TFA-method) to give 3-({4-Morpholin-4-yl-6-[4-(3-pyridin-4-yl-ureido)-phenyl]-[1,3,5]triazin-2-ylamino}-methyl)-azetidine-1-carboxylic acid tert-butyl ester (150 mg, 16% yield); MS (ESI) m/z 562.

Workup

  1. stirringthe reaction mixture was stirred for additional 1 hr
  2. customThe solvents were removed on a rotary evaporator
  3. customthe crude mixture was purified by semi-prep-HPLC (TFA-method)

Sources & evidence

ORD record
ord-0bd9c0a28806467b800096d1b6523337
Source dataset
uspto-grants-2013_05
Patent number
US08445486B2

Reaction notes

Loading…