Diisopropylethylamine → HCID 68158532, compound

HRID 243511Notes

Reaction equation

HRID 243511 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:10]2=[C:13]3[C:3]=1[O:4][CH2:5][C@H:6]([CH3:17])[N:7]3[C:8]([C@@H:14]([NH2:16])[CH3:15])=[N:9]2.[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23](Cl)[N:22]=[CH:21][N:20]=1.CCN(C(C)C)C(C)C>CC(O)C>[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23]([NH:16][C@H:14]([C:8]2[N:7]3[C:13]4[C:3]([O:4][CH2:5][C@@H:6]3[CH3:17])=[C:2]([F:1])[CH:12]=[CH:11][C:10]=4[N:9]=2)[CH3:15])[N:22]=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 68158448HCID 68158448, compound

Product 1

HCID 68158532HCID 68158532, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (S)-1-((S)-6-fluoro-3-methyl-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethylamine (86 mg, 0.36 mmol), 4-amino-6-chloro-5-cyanopyrimidine (56 mg, 0.36 mmol) and DIPEA (125 μL, 0.92 mmol) in IPA (1 mL) was heated for 18 h at 100° C. After cooling to RT, the volatiles were removed in vacuo and the resulting brown residue was purified by column chromatography (Si—PPC, gradient 0-5% 2M NH3/MeOH in DCM) to afford 440 as a white solid (100 mg, 79%). LCMS (Method K): RT 2.86 min [M+H]+ 354.1. 1H NMR (DMSO, 400 MHz): δ 8.01 (1H, s), 7.08 (1H, dd, J=8.8, 3.1 Hz), 6.94 (1H, dd, J=12.3, 8.8 Hz), 5.67 (1H, q, J=7.0 Hz), 5.04 (1H, qdd, J=6.6, 2.6, 1.7 Hz), 4.47 (1H, dd, J=11.9, 1.7 Hz), 4.20 (1H, dd, J=11.9, 2.6 Hz), 1.71 (3H, d, J=7.0 Hz), 1.45 (3H, d, J=6.6 Hz)

Workup

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed in vacuo
  3. customthe resulting brown residue was purified by column chromatography (Si—PPC, gradient 0-5% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-3175daed8079449cbe06e16d27ff4cfa
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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