HCID 58380528, compound → HCID 67345136, compound

HRID 1259407Notes

Reaction equation

HRID 1259407 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=2[F:16])=[C:6]([CH3:17])[C:5](=[O:18])[N:4]2[CH2:19][CH2:20][O:21][C:3]=12.[CH2:22]([O:29][CH2:30][CH:31]([CH:41]1[CH2:44][CH:43]([S:45](Cl)(=[O:47])=[O:46])[CH2:42]1)[CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[CH2:34]([O:33][CH2:32][CH:31]([CH:41]1[CH2:42][CH:43]([S:45]([NH:1][C:2]2[C:7]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=3[F:16])=[C:6]([CH3:17])[C:5](=[O:18])[N:4]3[CH2:19][CH2:20][O:21][C:3]=23)(=[O:47])=[O:46])[CH2:44]1)[CH2:30][O:29][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 58380528HCID 58380528, compoundHCID 583805443-(1,3-Bis(benzyloxy)propan-2-yl)cyclobutane-1-sulfonyl chloride

Product 1

HCID 67345136HCID 67345136, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using the same reaction conditions and procedure as described for the preparation of Example 7A, 8-Amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-2,3-dihydro-oxazolo[3,2-a]pyridin-5-one (I-7f: 0.22 g, 0.539 mmol) was reacted with 3-(1,3-bis(benzyloxy)propan-2-yl)cyclobutane-1-sulfonyl chloride (0.21 g, 0.539 mmol) in dry pyridine (2 mL) to afford the crude product. Purification by column chromatography on silica gel (80% ethyl acetate in hexane) afforded 0.3 g of the product (71% yield). LCMS: 80%, m/z=773 (M+1)

Workup

  1. customthe same reaction conditions and procedure
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (80% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-86c0cc247b6045e88268c6d62731d877
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

Loading…