Benzenesulfonic Acid → 5-(6-(7-methyl-2.3-dihydrobenzofuran-5-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[inden-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 2096373Notes

Reaction equation

C1(S(O)(=O)=O)C=CC=CC=1.[NH2:11][C:12]1[CH:13]=[C:14]2[C:27](=[CH:28][CH:29]=1)[CH2:26][C:16]1([C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]1=[O:25])[CH2:15]2.Cl[C:31]1[N:36]=[CH:35][N:34]=[C:33]([C:37]([C:39]2[CH:40]=[C:41]([CH3:48])[C:42]3[O:46][CH2:45][CH2:44][C:43]=3[CH:47]=2)=[O:38])[CH:32]=1>C(O)CCCC>[CH3:48][C:41]1[C:42]2[O:46][CH2:45][CH2:44][C:43]=2[CH:47]=[C:39]([C:37]([C:33]2[N:34]=[CH:35][N:36]=[C:31]([NH:11][C:12]3[CH:13]=[C:14]4[C:27](=[CH:28][CH:29]=3)[CH2:26][C:16]3([C:24]5[C:19](=[N:20][CH:21]=[CH:22][CH:23]=5)[NH:18][C:17]3=[O:25])[CH2:15]4)[CH:32]=2)=[O:38])[CH:40]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A spatula tip of benzenesulphonic acid was added to 70 mg (0.28 mmol) 5-amino-1,3-dihydrospiro[inden-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one and 0.10 g (0.26 mmol) (6-chloro-pyrimidin-4-yl)-(7-methyl-2,3-dihydro-benzofuran-5-yl)-methanone in 2 mL 1-pentanol and the mixture was stirred at 85° C. for 1 h. The reaction mixture was evaporated down, taken up in DMF, acidified with a few drops of hydrochloric acid and purified by preparative HPLC. The fractions containing the product were combined and freeze-dried.

Workup

customThe reaction mixture was evaporated down
custompurified by preparative HPLC
additionThe fractions containing the product
customfreeze-dried

Sources & evidence

ORD record: ord-ac8923d46a2a46eb9863b5b2f3f23e82
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450327B2

Reaction notes

Loading…