Methyl Isocyanate → HCID 44226678, compound

HRID 390158Notes

Reaction equation

HRID 390158 reaction equation
OC(C(F)(F)F)=O.[NH2:8][CH:9]1[C:36]2[C:31](=[C:32]([Br:37])[CH:33]=[CH:34][CH:35]=2)[C:11]2([CH2:16][CH2:15][N:14]([C:17](=[O:30])/[CH:18]=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])[CH2:13][CH2:12]2)[CH2:10]1.CCN(C(C)C)C(C)C.[CH3:47][N:48]=[C:49]=[O:50]>C(Cl)Cl>[Br:37][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:31]=1[C:11]1([CH2:16][CH2:15][N:14]([C:17](=[O:30])/[CH:18]=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:27])([F:28])[F:29])[CH2:13][CH2:12]1)[CH2:10][CH:9]2[NH:8][C:49]([NH:48][CH3:47])=[O:50]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 86654198HCID 86654198, compound

Product 1

HCID 44226678HCID 44226678, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vial equipped with a flea stirbar was charged with (±)-(E)-1-(3-amino-7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-yl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one TFA salt (9 mg, 0.015 mmol), i-Pr2NEt (0.01 mL) and CH2Cl2 (1 mL). MeNCO (0.05 mL, 0.085 mmol) was added. The mixture was stirred at rt for 3 h and evaporated to dryness. The residue was purified by prep HPLC to afford (±)-(E)-1-(7-bromo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)-3-methylurea (2.9 mg, 59%). LC-MS Method 1 tR=1.77, min, m/z=536, 538.

Workup

  1. customA vial equipped with a flea stirbar
  2. customevaporated to dryness
  3. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-afa8270ce1e5405886b7c343a1c849e2
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

Loading…