Triethylamine → HCID 60142390, compound

HRID 535899Notes

Reaction equation

HRID 535899 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[CH:17][C:16]=2[O:27][CH3:28])[C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=1.C(N(CC)CC)C.Cl.Cl[CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1>O1CCCC1>[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][N:24]([CH2:43][CH2:44][N:45]4[CH2:50][CH2:49][O:48][CH2:47][CH2:46]4)[CH2:23][CH2:22]3)=[CH:17][C:16]=2[O:27][CH3:28])[C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 70498277HCID 70498277, compound

Product 1

HCID 60142390HCID 60142390, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of EXAMPLE 42B (25 mg, 0.053 mmol) in tetrahydrofuran (1 mL), triethylamine (22.24 uL, 0.16 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (9.9 mg, 0.053 mmol) were heated to 75° C. over 18 hours. The reaction mixture was concentrated under reduced pressure and purified on RP-HPLC (10 mM ammonium acetate/acetonitrile) to afford the title compound. 1H NMR (CDCl3) δ ppm 9.76 (s, 1H), 7.88 (s, 1H), 7.76 (s, 1H), 7.23-7.06 (m, 4H), 7.06-6.91 (m, 1H), 6.58-6.53 (d, J=2.5, 6H), 6.47 (dd, J=8.6, 2.5, 5H), 5.46 (s, 1H), 4.02 (d, J=1.9, 2H), 3.83-3.68 (m, 7H), 3.27-3.09 (m, 4H), 2.77-2.49 (m, 12H); MS (ESI) m/z 584 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified on RP-HPLC (10 mM ammonium acetate/acetonitrile)

Sources & evidence

ORD record
ord-9c50a10c198e4ae9880cac4da5385649
Source dataset
uspto-grants-2014_10
Patent number
US08859546B2

Reaction notes

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