Carbonic acid-guanidine (1:1) → 5-[4-(2-Fluorobenzyl)cyclohexylmethoxy]quinazoline-2,4-diamine

HRID 1015365Notes

Reaction equation

HRID 1015365 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH:12]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[CH2:14][CH2:13]2)[C:3]=1[C:4]#[N:5].C(=O)(O)O.[NH2:30][C:31]([NH2:33])=[NH:32]>>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][CH:15]1[CH2:14][CH2:13][CH:12]([CH2:11][O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:2]3[C:3]=2[C:4]([NH2:5])=[N:32][C:31]([NH2:33])=[N:30]3)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 673013762-Fluoro-6-[4-(2-fluorobenzyl)cyclohexylmethoxy]benzonitrile

Product 1

HCID 250034795-[4-(2-Fluorobenzyl)cyclohexylmethoxy]quinazoline-2,4-diamineYield 52%

Procedure

Cyclization of 2-fluoro-6-[4-(2-fluorobenzyl)cyclohexylmethoxy]benzonitrile (225 mg; 0.66 mmol) and guanidine carbonate (119 mg; 0.66 mmol) was carried out using Method F. Material was purified using ethyl alcohol trituration. Solids were collected by filtration. Title compound was obtained. (130 mg; 52% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.33 (t, J=8.0 Hz, 1H), 7.24 (m, 4H), 7.12 (m, 2H), 6.75 (dd, J=8.4, 0.8 Hz, 1H), 6.51 (d, J=7.6 Hz, 1H), 5.97 (br s, 2H), 3.92 (d, J=5.6 Hz, 2H), 2.52 (d, J=7.2 Hz, 2H), 1.83 (m, 3H), 1.69 (m, 2H), 1.51 (m, 1H), 1.06 (m, 4H). MS m/z (APCI) 381 (M+H)+.

Workup

  1. customMaterial was purified
  2. filtrationSolids were collected by filtration

Sources & evidence

ORD record
ord-e683641bb5384eaeadbb76b7550ebed1
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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