Carbonic acid-guanidine (1:1) → HCID 25003846, compound

HRID 1015376Notes

Reaction equation

HRID 1015376 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][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.[NH2:30][C:31]([NH2:33])=[NH:32]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][CH:5]1[CH2:6][CH2:7][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:32][C:31]([NH2:33])=[N:30]3)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 67301356HCID 67301356, compound

Product 1

HCID 25003846HCID 25003846, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Cyclization of 2-[4-(2-chlorobenzyl)cyclohexylmethoxy]-6-fluorobenzonitrile (100 mg; 0.28 mmol) was carried out using Method F using guanidine carbonate (100 mg; 0.55 mmol) in 1.5 mL of dimethylacetamide. Title compound was obtained as a white solid. (88 mg; 79% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.27 (m, 7H), 6.75 (d, J=8.0 Hz, 1H), 6.50 (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), 1.68 (m, 3H), 1.06 (m, 4H). MS m/z (ESI) 398 (M+H)+.

Sources & evidence

ORD record
ord-00551541855046b3bf99bf81e6000458
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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