Ammonia → HCID 178472387, compound

HRID 1028795Notes

Reaction equation

HRID 1028795 reaction equation
[NH3:1].[CH2:2]([O:4][C:5]([C@H:7]1[CH2:12][CH2:11][C@@H:10]([N:13]2[C:17]3[N:18]=[CH:19][N:20]=[C:21](Cl)[C:16]=3[C:15]([I:23])=[CH:14]2)[CH2:9][CH2:8]1)=[O:6])[CH3:3]>CC(O)C>[CH2:2]([O:4][C:5]([C@H:7]1[CH2:12][CH2:11][C@@H:10]([N:13]2[C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH2:1])[C:16]=3[C:15]([I:23])=[CH:14]2)[CH2:9][CH2:8]1)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178472386HCID 178472386, compound

Product 1

HCID 178472387HCID 178472387, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
-78 °C

Procedure

Gaseous ammonia was bubbled into an iPrOH (1 mL) solution of cis-4-(4-chloro-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-cyclohexanecarboxylic acid ethyl ester (30 mg, 70% pure by HPLC peak area, 0.048 mmol) in a glass pressure tube, cooled to −78° C. in a dry ice/acetone bath, for 15 min. The tube was equipped with a Teflon washer, sealed and heated to 110° C. for 7 h. After that time, the excess NH3 and the solvent were evaporated. The residue was used for the next reaction without purification. A portion of above crude material were purified by HPLC to give the title compound as pale yellow oil. 1H NMR (CDCl3, 400 MHz): δ=1.31 (t, 3H, J=7.6 Hz), 1.63-1.98 (m, 6H), 2.29-2.35 (m, 2H), 2.73 (m, 1H), 4.22 (q, 2H, J=7.6 Hz), 4.64-4.71 (m, 1H), 5.58 (brs, 2H), 7.11 (s, 1H), 8.26 (s, 1H). MS (ES+): 415.0 [MH+]. tR=2.7 min (polar—5 min).

Workup

  1. customsealed
  2. temperatureheated to 110° C. for 7 h
  3. customAfter that time, the excess NH3 and the solvent were evaporated
  4. customThe residue was used for the next reaction without purification
  5. customA portion of above crude material were purified by HPLC

Sources & evidence

ORD record
ord-e4d8bc1d2c4c41ca831e1dfeeeb9490d
Source dataset
uspto-grants-2014_05
Patent number
US08735405B2

Reaction notes

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