Pyridine → Sufugolix

HRID 23256Notes

Reaction equation

HRID 23256 reaction equation
Cl.[CH3:2][O:3][NH2:4].N1C=CC=CC=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:43][C:21]3[N:22]([CH2:34][C:35]4[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=4[F:42])[C:23](=[O:33])[N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:25](=[O:26])[C:20]=3[C:19]=2[CH2:44][N:45]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH3:46])=[CH:14][CH:13]=1.C(N(CC)CC)C.C[C:62](N(C)C)=[O:63]>O>[CH2:47]([N:45]([CH2:44][C:19]1[C:20]2[C:25](=[O:26])[N:24]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:23](=[O:33])[N:22]([CH2:34][C:35]3[C:36]([F:42])=[CH:37][CH:38]=[CH:39][C:40]=3[F:41])[C:21]=2[S:43][C:18]=1[C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:62]([NH:4][O:3][CH3:2])=[O:63])=[CH:17][CH:16]=1)[CH3:46])[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 31374DimethylacetamideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 109190521-(2,6-difluorobenzyl)-6-(4-aminophenyl)-5-((benzyl(methyl)amino)methyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 3038517Sufugolix

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

O-methylhydroxylamine hydrochloride (351 mg, 4.20 mmol) was dissolved in dimethylacetamide (2 ml), pyridine (340 μl, 4.20 mmol) and phenyl chloroformate (phenyl chlorocarbonate)(527 μl, 4.20 mmol) were added thereto successively dropwise, and the mixture was stirred at room temperature for 20 minutes. 6-(4-aminophenyl)-5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H, 3H)-dione (500 mg, 0.84 μmol) and triethylamine (1.29 ml, 9.25 mmol) were added thereto, and the mixture was stirred at 50° C. for 18 hours. Water (40 ml) was added thereto, and the mixture was stirred vigorously. The crystals were filtered, and dried under vacuum at 40° C. to give white crystals of 5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-(3-methoxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4(1H, 3H)-dione (0.58 g) quantitatively.

Workup

  1. stirringthe mixture was stirred at 50° C. for 18 hours
  2. stirringthe mixture was stirred vigorously
  3. filtrationThe crystals were filtered
  4. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-2fe03ac7be034390a160546ff30fdda1
Source dataset
uspto-grants-2005_02
Patent number
US06849738B2

Reaction notes

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