Diisopropylethylamine → HCID 66586889, compound

HRID 625438Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:4][C:3]=1[C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][N:31]=1)[C:16]([NH:18][C@@H:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][CH2:20]1)=[O:17].[C:32]([O:36][C:37]([C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][CH:47]=1)[C:42](O)=[O:43])=[O:38])([CH3:35])([CH3:34])[CH3:33].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[CH2:9]([N:8]([CH2:11][CH3:12])[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:42]([C:41]2[CH:40]=[C:39]([CH:47]=[CH:46][CH:45]=2)[C:37]([O:36][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:38])=[O:43])=[C:3]([C:13]2[CH:14]=[C:15]([C:16](=[O:17])[NH:18][C@@H:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21][CH2:20]3)[CH:29]=[CH:30][N:31]=2)[CH:4]=1)[CH3:10]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of (S)-2-(2-amino-5-(diethylamino)phenyl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isonicotinamide (7.1 mmol, 2.94 g), 3-(tert-butoxycarbonyl)benzoic acid (8.52 mmol, 1.89 g) and DIEA (35.5 mmol, 4.59 g) in DMF (16 mL) was added HATU (8.52 mmol, 3.24 g). The mixture was stirred at 60° C. for 1 h. The reaction mixture was diluted with ethyl acetate, washed with water (2×), brine (1×), dried and concentrated. The residue was purified by column to give a yellow solid (4.31 g, 98%).

Workup

washwashed with water (2×), brine (1×)
customdried
concentrationconcentrated
customThe residue was purified by column

Sources & evidence

ORD record: ord-cc0eb1c795924efd89d304fb6db0973d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09301951B2

Reaction notes

Loading…