Ammonium Hydroxide → HCID 482344, compound

HRID 2393284Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]=[CH:7][N:6]([C@H:13]([CH3:30])[C@:14]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[F:29])([OH:21])[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:5]2=[O:31].[NH4+:32].[OH-]>>[NH2:32][C:11]1[CH:10]=[C:9]2[C:4]([C:5](=[O:31])[N:6]([C@H:13]([CH3:30])[C@:14]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=3[F:29])([OH:21])[CH2:15][N:16]3[CH:20]=[N:19][CH:18]=[N:17]3)[CH:7]=[N:8]2)=[CH:3][C:2]=1[F:1]

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 482334HCID 482334, compound

Product 1

HCID 482344HCID 482344, compound

Procedure

Following a similar procedure to that described in example 40 but using (1R,2R)-6,7-difluoro-3-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]quinazolin-4(3H)-one (obtained in example 15) and NH4OH the title compound was obtained as a white solid: mp 124°-125° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.45 (s, 1H, N=CH--N), 7.86 (d, J=11, 1H, arom), 7.76 (s, 1H, triazole), 7.72 (s, 1H, triazole), 7.6-7.4 (m, 1H, arom), 6.97 (d, J=8.0, 1H, arom), 6.9-6.7 (m, 2H, arom), 5.89 (dq, Jd =1.7, Jq =7.3, 1H, MeCH), 5.46 (d, J=1.7, 1H, OH), 5.15 (d, J=14.2, 1H, CH(H)), 4.43 (broad s, 2H, NH2), 4.01 (d, J=14.2, 1H, CH(H)), 1.26 (d, J=7.3, 3H, CHMe); GC/MS 224 (Tr--CH2COHAr, C10H8F2N3O), 207 (N-ethylheterocycle, C10H10FN3O); [α]D =-0.31° (c 1, MeOH). Analysis calculated for C20H17 F3N6O2.H2O: C 53.57; H 4.27; N 18.74. Found: C 54.16; H 4.29; N 17.42.

Sources & evidence

ORD record: ord-f46a506772c34c6cb5a1527441a27ec5
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05807854

Reaction notes

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