HCID 86684322, compound → HCID 86567321, compound

HRID 1411699Notes

Reaction equation

HRID 1411699 reaction equation
[CH3:1][C:2]1([CH3:39])[CH2:13][C:12]2[CH:11]=[C:10]3[N:5]([CH2:6][CH2:7][N:8]([C:15]4[C:20]([CH:21]=[O:22])=[C:19]([C:23]5[CH:28]=[C:27]([NH:29][C:30]6[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32][N:31]=6)[C:26](=[O:37])[N:25]([CH3:38])[CH:24]=5)[CH:18]=[CH:17][N:16]=4)[C:9]3=[O:14])[C:4]=2[CH2:3]1>O>[OH:22][CH2:21][C:20]1[C:15]([N:8]2[CH2:7][CH2:6][N:5]3[C:4]4[CH2:3][C:2]([CH3:1])([CH3:39])[CH2:13][C:12]=4[CH:11]=[C:10]3[C:9]2=[O:14])=[N:16][CH:17]=[CH:18][C:19]=1[C:23]1[CH:28]=[C:27]([NH:29][C:30]2[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32][N:31]=2)[C:26](=[O:37])[N:25]([CH3:38])[CH:24]=1

Participants

3

Reactant 1

HCID 86684322HCID 86684322, compound

Product 1

HCID 86567321HCID 86567321, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At 0° C., to a solution of 180c with water (1 mL). It was then concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 180 (47 mg, 32%). MS-ESI: [M+H]+ 526.2. 1H NMR (500 MHz, CDCl3) δ 8.82 (d, J=2.5 Hz, 1H), 8.68 (s, 1H), 8.51 (d, J=2.5 Hz, 1H), 8.02-8.00 (m, 2H), 7.35 (d, J=5.0 Hz, 1H), 6.84 (s, 1H), 6.62 (s, 1H), 5.13 (t, J=6.5 Hz, 1H), 4.67-4.52 (m, 2H), 4.29-4.15 (m, 3H), 3.88-3.86 (m, 1H), 3.72 (s, 3H), 2.57 (d, J=5.5 Hz, 2H), 2.51 (s, 2H), 2.43 (s, 3H), 1.28 (s, 6H).

Workup

  1. customAt 0° C.
  2. concentrationIt was then concentrated under reduced pressure
  3. customthe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-082348fee38640d09b473943af5ef630
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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