Diisopropylamine → HCID 59553173, compound

HRID 1171366Notes

Reaction equation

HRID 1171366 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH2:20])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([N:31]2[CH2:36][CH2:35][CH:34]([CH3:37])[CH2:33][CH2:32]2)[CH:30]=1)[C:25](O)=[O:26].CC1CCNCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NC(C)C)(C)C>CN(C=O)C.C(Cl)Cl>[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([N:31]2[CH2:36][CH2:35][CH:34]([CH3:37])[CH2:33][CH2:32]2)[CH:30]=1)[C:25]([NH:20][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([O:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:11][CH:12]=1)=[O:26]

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 693814-MethylpiperidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 110439124-(2-Morpholinoethoxy)naphthalen-1-amineHCID 595533113-Fluoro-5-(4-methylpiperidin-1-yl)benzoic acid

Product 1

HCID 59553173HCID 59553173, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(2-morpholin-4-ylethoxy)-1-naphthyl]amine (0.60 g, 2.2 mmol) in DMF (2 ml) is added 3-fluoro-5-(4-methylpiperidin-1-yl)benzoic acid (0.63 g, 2.64 mmol), prepared from 4-methylpiperidine according to conditions described in general procedure E, HBTU (1.25 g, 3.3 mmol) and diisopropylamine (1.15 ml, 6.6 mmol). This mixture is stirred at room temperature overnight and diluted with CH2Cl2 (5 ml), washed with 0.05 N NaOH, dried over Na2SO4 and concentrated. The residue is purified by column chromatography on silica gel (90% EtOAc in hexane) to give 3-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2-morpholin-4-ylethoxy)-1-naphthyl]benzamide as a white solid (0.53 g). Mp: 116-118° C.; 1H NMR (300 MHz, DMSO-d6) δ 0.91 (d, 6.3 Hz, 3H), 1.15-1.25 (m, 2H), 1.67 (d, J=12 Hz, 2H), 2.55 (bs, 4H), 2.74 (t, J=12.3 Hz, 2H), 2.86 (s, 2H), 3.59 (t, J=4.5 Hz, 4H), 3.82 (d, J=12.9 Hz, 2H), 4.29 (t, J=5.7 Hz, 2H), 6.93 (d, J=12.6 Hz, 1H), 7.00 (d, J=8.1Hz, 1H), 7.12 (d, J=8.7 Hz, 1H), 7.37-7.43 (m, 2H), 7.51-7.55 (m, 2H), 7.81-7.84 (m, 1H), 8.17-8.20 (m, 1H), 10.21 (s, 1H); MS 492 (M+1).

Workup

  1. washwashed with 0.05 N NaOH
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography on silica gel (90% EtOAc in hexane)

Sources & evidence

ORD record
ord-d74b36897d1e499ca006e79d1670b790
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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