Carbonic acid-guanidine (1:1) → HCID 25003844, compound

HRID 1015371Notes

Reaction equation

HRID 1015371 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][O:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:17](F)[C:14]=2[C:15]#[N:16])[CH2:7][CH2:6]1.C(=O)(O)O.[NH2:31][C:32]([NH2:34])=[NH:33]>CC(N(C)C)=O>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][O:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:14]=2[C:15]([NH2:16])=[N:31][C:32]([NH2:34])=[N:33]3)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 67301337HCID 67301337, compound

Product 1

HCID 25003844HCID 25003844, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Cyclization of 2-[4-(2,6-difluorophenoxy)cyclohexylmethoxy]-6-fluorobenzonitrile was carried out using Method F (95 mg; 0.26 mmol) and guanidine carbonate (43 mg; 0.26 mmol) in 1.5 mL of dimethylacetamide. Material was purified using C18 reverse phase silica and 0-100% acetonitrile in water gradient to give 9 mg of title compound. (9% yield. 1HNMR (400 MHz, DMSO-d6) δ 7.37 (m, 1H), 7.14 (m, 5H), 6.77 (m, 1H), 6.51 (m, 1H), 5.96 (br s, 2H), 5.7 (s, 1H), 4.02 (m, 3H), 2.02 (m, 4H), 1.62 (m, 4H). MS m/z (ESI) 401 (M+H)+.

Workup

  1. customMaterial was purified

Sources & evidence

ORD record
ord-bdcd0a34c19442068350c9b178e38b4d
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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