Diisopropylamine → HCID 178508832, compound

HRID 1099309Notes

Reaction equation

HRID 1099309 reaction equation
ClC1C=CC([N:8]([C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][N:13]=2)[C:9](=O)[O-:10])=CC=1.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:30]=[C:31]([CH2:39][N:40]3[CH2:46][CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[N:32]3[C:37]=2[C:36]([NH2:38])=[N:35][CH:34]=[N:33]3)=[CH:25][C:24]=1[F:47].C(NC(C)C)(C)C.[O:55]1CCOCC1>>[NH2:38][C:36]1[C:37]2=[C:29]([C:26]3[CH:27]=[CH:28][C:23]([NH:22][C:9]([NH:8][C:12]4[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][N+:13]=4[O-:55])=[O:10])=[C:24]([F:47])[CH:25]=3)[CH:30]=[C:31]([CH2:39][N:40]3[CH2:46][CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[N:32]2[N:33]=[CH:34][N:35]=1

Participants

5

Reactant 4

HCID 7912DiisopropylamineHCID 312751,4-DioxaneHCID 66589392HCID 66589392, compoundHCID 86639791HCID 86639791, compound

Product 1

HCID 178508832HCID 178508832, compoundYield 24%

Conditions

Temperature
80 °C

Procedure

4-chlorophenyl[4-(trifluoromethyl)pyridin-2-yl]carbamate (35 mg, 0.098 mmol) and 5-(4-amino-3-fluorophenyl)-7-(1,4-oxazepan-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (36 mg, 0.11 mmol) were combined in 1,4-dioxane (1 mL) and treated with N,N-diisopropylamine (34 mL, 0.20 mmol). The reaction was heated to 80° C. overnight. The reaction was then concentrated and purified over silica (0-20%, MeOH/CH2Cl2) to yield an orange solid (13 mg, 24%). 1H-NMR (DMSO-d6) 10.83 (d, J=5.1 Hz, 1 H), 10.09 (s, 1H), 8.61 (d, J=2.4 Hz, 1 H), 8.57 (d, J=6.6 Hz, 1 H), 8.22 (td, J1=9.2 Hz, J2=2.4 Hz, 1 H), 7.92 (s, 1 H), 7.44 (dd, J1=6.7 Hz, J2=2.9 Hz, 1 H), 7.36 (dd, J1=12.1 Hz, J2=2.0 Hz, 1 H), 7.27 (dd, J1=8.3 Hz, J2=1.6 Hz, 1 H), 6.69 (s, 1 H), 3.99 (s, 2 H), 3.67 (t, J=6.0 Hz, 2 H), 3.61-3.59 (m, 2 H), 2.75-2.68 (m, 4 H), 1.80 (q, J=5.7 Hz, 2 H); MS [M+H]+=561.0; LCMS RT=1.62 min.

Workup

  1. concentrationThe reaction was then concentrated
  2. custompurified over silica (0-20%, MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9bb821c1d9784d34834989cfc529dbc4
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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