6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one → HCID 25253370, compound

HRID 914072Notes

Reaction equation

HRID 914072 reaction equation
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21]C4C=CC(C(O)=O)=CC=4OC)=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1N=CC2N(C)C(=O)C(F)(F)CN(C3CCCC3)C=2N=1.N[C:55]1[CH:65]=[CH:64][C:58]2[O:59][CH2:60][C:61](=[O:63])[NH:62][C:57]=2[CH:56]=1>>[CH:1]1([N:6]2[CH2:12][C:11]([F:13])([F:14])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:55]4[CH:65]=[CH:64][C:58]5[O:59][CH2:60][C:61](=[O:63])[NH:62][C:57]=5[CH:56]=4)=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 27636816-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 252529054-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acidHCID 579555742-Chloro-9-cyclopentyl-7,7-difluoro-5-methyl-8,9-dihydro-5H-pyrimido[4,5-B][1,4]diazepin-6(7H)-one

Product 1

HCID 25253370HCID 25253370, compound

Procedure

The title compound was synthesized using an analogous procedure to that described in connection with 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid from 2-Chloro-9-cyclopentyl-7,7-difluoro-5-methyl-8,9-dihydro-5H-pyrimido[5,4-b][1,4]diazepin-6(7H)-one and 6-amino-2H-benzo[b][1,4]oxazin-3(4H)-one. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.48-1.80 (m, 6H) 1.95 (br. s, 2H) 3.40 (s, 3H) 4.01 (t, J=14.15 Hz, 2H) 4.52 (s, 2H) 4.72 (t, J=8.08 Hz, 1H) 6.77 (d, J=8.34 Hz, 1H) 7.20 (dd, J=8.59, 2.02 Hz, 1H) 7.46 (d, J=2.27 Hz, 1H) 8.20 (s, 1H) 9.35 (s, 1H) 10.54 (br. s., 1H) [M+H] calc'd for C21H22F2N6O3, 445. found 445.

Sources & evidence

ORD record
ord-4ba0301305744b2bb8b165699e43975f
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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