Hydrochloric Acid → 4-methyl-6-(6-(2'-oxo-1.1'.2'.3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one

HRID 1846531Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.Cl[C:21]1[N:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]2[CH:37]=[C:36]([CH3:38])[C:31]3[NH:32][C:33](=[O:35])[O:34][C:30]=3[CH:29]=2)[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN1C(=O)CCC1.O.CN(C=O)C>[CH3:38][C:36]1[C:31]2[NH:32][C:33](=[O:35])[O:34][C:30]=2[CH:29]=[C:28]([NH:27][C:23]2[CH:22]=[C:21]([NH:1][C:2]3[CH:3]=[C:4]4[C:17](=[CH:18][CH:19]=3)[CH2:16][C:6]3([C:14]5[C:9](=[N:10][CH:11]=[CH:12][CH:13]=5)[NH:8][C:7]3=[O:15])[CH2:5]4)[N:26]=[CH:25][N:24]=2)[CH:37]=1

Participants

Conditions

Temperature: 130 °C

Procedure

57 mg (0.23 mmol) 5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one, 80 mg (0.23 mmol) 6-(6-chloro-pyrimidin-4-ylamino)-4-methyl-3H-benzoxazol-2-one and 69 mg (0.50 mmol) potassium carbonate were combined in 1.5 mL NMP and stirred for 2 h at 130° C. Then the reaction mixture was cooled, acidified with 1M aqueous hydrochloric acid solution and stirred for 1 h at 50° C. The reaction mixture was diluted with water, the precipitate was taken up in DMF and purified by preparative HPLC. The product-containing fractions were combined and freeze-dried.

Workup

temperatureThen the reaction mixture was cooled
stirringstirred for 1 h at 50° C
custompurified by preparative HPLC
customfreeze-dried

Sources & evidence

ORD record: ord-1cb3adddc6a84d27a683210f2ae11de3
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952014B2

Reaction notes

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