Nitrogen → HCID 59380443, compound

HRID 2353847Notes

Reaction equation

HRID 2353847 reaction equation
N#N.[Cl:3][C:4]1[CH:5]=[C:6]([NH:19][C:20]2[C:21]3[C:28]4[CH:29]=[CH:30][C:31](/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36])=[CH:32][C:27]=4[S:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([NH:19][C:20]2[C:21]3[C:28]4[CH:29]=[CH:30][C:31]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[CH:32][C:27]=4[S:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1

Participants

4

Reactant 2

HCID 947NitrogenHCID 59380396HCID 59380396, compound

Product 1

HCID 59380443HCID 59380443, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a blanket of N2 10% Pd—C (4 mg)) was added to a flask which was flushed with N2 and the catalyst was wet with THF. A solution of (2E)-3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-yl]acrylic acid (40 mg, 0.08 mmol) in THF (2 mL) was also added to the above flask. The flask was vacuumed and H2 was introduced into it. The reaction mixture was stirred under H2 at rt for 16 h. The Pd—C was carefully filtered and the filtrate was concentrated to yield a white solid (30 mg, 75%). 1H-NMR (DMSO-d6) δ 8.95 (s, 1H), 8.50 (s, 1H), 8.45 (d, 1H), 7.96 (s, 1H), 7.74 (d, 1H), 7.52 (dd, 1H), 7.45 (m, 2H), 7.30 (m, 2H), 7.24 (d, 1H), 7.16 (m, 1H), 5.26 (s, 2H), 2.99 (t, 2H), 2.59 (t, 2H); LCMS RT=3.73 min, [M+H]+=508.1.

Workup

  1. customwas flushed with N2
  2. additionH2 was introduced into it
  3. filtrationThe Pd—C was carefully filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7553f7709123428a897aac638ec77483
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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