Ethyl isocyanate → HCID 67325351, compound

HRID 1616895Notes

Reaction equation

HRID 1616895 reaction equation
C(OC(N1CC[CH:11]2[C:14]3[CH:20]=[CH:19][C:18]([S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=4)(=[O:23])=[O:22])=[CH:17][C:15]=3[O:16]C2C1)=O)(C)(C)C.[CH2:31]([N:33]=[C:34]=[O:35])[CH3:32].C([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])C>>[CH2:31]([NH:33][C:34](=[O:35])[O:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([S:21]([C:18]2[CH:19]=[CH:20][C:14]3[CH:11]4[CH2:40][CH2:39][NH:38][CH2:41][CH:42]4[O:16][C:15]=3[CH:17]=2)(=[O:22])=[O:23])[CH:25]=1)[CH3:32]

Participants

4

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 53327613HCID 53327613, compound

Product 1

HCID 67325351HCID 67325351, compound

Procedure

A mixture of 7-(3-hydroxy-benzenesulfonyl)-3,4,4a,9a-tetrahydro-1H-benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester (30 mg, 0.07 mmol), ethyl isocyanate (0.5 ml, excess) and triethylamine (0.5 mL, excess) was stirred at r.t. After 18 h, the mixture was filtered, and the filtrate evaporated. Purification by preparative TLC (hexane:EtOAc 40:60) followed by removal of N-Boc protecting group with 4N HCl using a general procedure afforded the title product. mp 217-219° C., MS m/z 403 [M+H]+. 1H-NMR (400 MHz, DMSOd6): δ 8.97 (br s, 1H), 7.80 (d, J=7.96 Hz, 1H), 7.62 (s, 1H), 7.60-7.55 (m, 3H), 7.43 (overlapping s and d, 2H), 4.95 (m, 1H), 3.57 (m, 2H), 3.44 (m, 1H), 3.14 (m, 2H), 2.94 (m; 2H), 2.55 (s, 2H), 2.12 (m, 1H), 1.52 (m, 1H), 1.09 (t, 3H).

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate evaporated
  3. customPurification by preparative TLC (hexane:EtOAc 40:60)
  4. customfollowed by removal of N-Boc protecting group with 4N HCl using a general procedure

Sources & evidence

ORD record
ord-5494fa6d2655406fb3cad2a022f6d3c2
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

Loading…