Potassium Carbonate → HCID 10371129, compound

HRID 1372174Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([NH:21][S:22]([C:25]2[S:34][C:28]3=[N:29][C:30]([Cl:33])=[CH:31][CH:32]=[C:27]3[CH:26]=2)(=[O:24])=[O:23])[C:16]1=[O:35].Br[CH2:37][C:38]([O:40][CH3:41])=[O:39].C(=O)([O-])[O-].[K+].[K+]>>[CH3:41][O:40][C:38](=[O:39])[CH2:37][N:21]([S:22]([C:25]1[S:34][C:28]2=[N:29][C:30]([Cl:33])=[CH:31][CH:32]=[C:27]2[CH:26]=1)(=[O:24])=[O:23])[CH:17]1[CH2:18][CH2:19][CH2:20][N:15]([C:3]2[CH:4]=[CH:5][C:6]([N:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]3=[O:14])=[CH:7][CH:2]=2)[C:16]1=[O:35]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 60984Methyl bromoacetate

HCID 10098572HCID 10098572, compound

Product 1

HCID 10371129HCID 10371129, compound

Procedure

The compound of Example 3 was treated with methyl bromoacetate in the presence of potassium carbonate using the procedure described for the preparation of compound 9, Part A. Purification by flash chromatography provided the title compound. MS(ESI+) (M+H)+. 1HNMR (CDCl3) δ 8.08 (m, 1H); 7.89 (s, 1H); 7.48 (m, 1H); 7.39 (m, 2H); 7.31 (m, 4H); 6.78 (m, 1H); 6.36 (m, 1H); 4.72 (m, 1H); 4.27 (m, aH); 3.83 (m, 1H); 3.78 (s, 3H); 3.74 (m, 1H); 3.66 (m, 1H); 2.60 (m, 1H); 2.16 (m, 3H). MS m/z 586.9 (M+H)+. HRMS calcd for C26H24N4O6S2Cl: 587.0826. Found: 587.0813.

Workup

customPurification by flash chromatography

Sources & evidence

ORD record: ord-3f8923cdded54e70b93a2e3064f7dd11
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157470B2

Reaction notes

Loading…