2-chloro-9-cyclopentyl-8,9-dihydro-5-methylspiro[5H-pyrimido[4,5-b][1,4]diazepine-7,1'-cyclopropan]-6(7H)-one → 4-(9'-cyclopentyl-5'-methyl-6'-oxo-5',6',8',9'-tetrahydrospiro[cyclopropane-1,7'-pyrimido[5,4-b][1,4]diazepine]-2'-ylamino)-N-[(3R)-1-ethylpyrrolidin-3-yl]-3-methoxy-benzamide

HRID 2234329Notes

Reaction equation

HRID 2234329 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH3:21])[C:7](=[O:20])[C:8]3([CH2:19][CH2:18]3)[CH2:9][N:10]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:11]=2[N:12]=1.[NH2:22][C:23]1[CH:38]=[CH:37][C:26]([C:27]([NH:29][C@@H:30]2[CH2:34][CH2:33][N:32]([CH2:35][CH3:36])[CH2:31]2)=[O:28])=[CH:25][C:24]=1[O:39][CH3:40]>>[CH:13]1([N:10]2[CH2:9][C:8]3([CH2:19][CH2:18]3)[C:7](=[O:20])[N:6]([CH3:21])[C:5]3[CH:4]=[N:3][C:2]([NH:22][C:23]4[CH:38]=[CH:37][C:26]([C:27]([NH:29][C@@H:30]5[CH2:34][CH2:33][N:32]([CH2:35][CH3:36])[CH2:31]5)=[O:28])=[CH:25][C:24]=4[O:39][CH3:40])=[N:12][C:11]2=3)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 579699392-chloro-9-cyclopentyl-8,9-dihydro-5-methylspiro[5H-pyrimido[4,5-b][1,4]diazepine-7,1'-cyclopropan]-6(7H)-one2×HCID 686854984-amino-N-[(3R)-1-ethylpyrrolidin-3-yl]-3-methoxy-benzamide2×

Product 1

HCID 686830904-(9'-cyclopentyl-5'-methyl-6'-oxo-5',6',8',9'-tetrahydrospiro[cyclopropane-1,7'-pyrimido[5,4-b][1,4]diazepine]-2'-ylamino)-N-[(3R)-1-ethylpyrrolidin-3-yl]-3-methoxy-benzamide

Procedure

The title compound was prepared by an analogous method to the preparation of Example 350, utilising, 2′-chloro-9′-cyclopentyl-5′-methyl-8′,9′-dihydrospiro[cyclopropane-1,7′-pyrimido[5,4-b][1,4]diazepin]-6′(5′H)-one (Intermediate 130; 75 mg, 0.24 mmol), and 4-amino-N-[(3R)-1-ethylpyrrolidin-3-yl]-3-methoxy-benzamide (Intermediate 245; 70 mg, 0.26 mmol) heating by microwave irradiation at 160° C. for 1 hour, as an off-white foam (50 mg, 39%).

Sources & evidence

ORD record
ord-4b869e7a6ff149098af723de07006464
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

Loading…