Diisopropylethylamine → HCID 57410483, compound

HRID 1502305Notes

Reaction equation

HRID 1502305 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1.[O:20]1[CH2:25][CH2:24][CH:23]([C:26](O)=[O:27])[CH2:22][CH2:21]1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>ClCCl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][C:26]([CH:23]4[CH2:24][CH2:25][O:20][CH2:21][CH2:22]4)=[O:27])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 219302Oxane-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 574102447-(5-Fluoro-2-methylphenyl)isoquinolin-3-amine

Product 1

HCID 57410483HCID 57410483, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

7-(5-Fluoro-2-methylphenyl)isoquinolin-3-amine (150 mg, 0.595 mmol), tetrahydro-2H-pyran-4-carboxylic acid (1.43 mmol, 185 mg), N,N-diisopropylethylamine (384 mg, 2.98 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (543 mg, 1.43 mmol) were dissolved in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 48 hours. Water (1 mL) was added, and the mixture was concentrated, washed with methanol to give the product (45.2 mg, 21.0%). LCMS (ESI): RT (Min)=1.203, M+H+=365.0, method=A; 1H NMR (400 MHz, DMSO-d6) δ 10.60 (s, 1H), 9.15 (s, 1H), 8.52 (s, 1H), 8.02 (s, 1H), 7.93 (d, J=8.8 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.36 (s, 1H), 7.14 (d, J=12.0 Hz, 2H), 3.92-3.88 (m, 2H), 3.36-3.32 (m, 2H), 2.81-2.80 (m, 1H), 2.23 (s, 3H), 1.71-1.66 (m, 4H).

Workup

  1. concentrationthe mixture was concentrated
  2. washwashed with methanol

Sources & evidence

ORD record
ord-24b244b06c5e4d408dad917cfab20503
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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