Sodium dicyanamide → HCID 178496720, compound

HRID 571364Notes

Reaction equation

HRID 571364 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][C@@H:10]2[CH2:17][C@H:13]3[CH2:14][NH:15][CH2:16][C@@:12]3([C:18]([N:20]3[CH2:29][CH2:28][C:27]4[N:26]=[CH:25][C:24]([C:30]([F:33])([F:32])[F:31])=[CH:23][C:22]=4[CH2:21]3)=[O:19])[CH2:11]2)[CH2:7][CH2:6][O:5][CH2:4]1.[N-:34]([C:37]#[N:38])[C:35]#[N:36].[Na+]>O.CC(O)C.C(Cl)Cl>[C:35](/[N:34]=[C:37](/[N:15]1[CH2:16][C@@:12]2([C:18]([N:20]3[CH2:29][CH2:28][C:27]4[N:26]=[CH:25][C:24]([C:30]([F:33])([F:31])[F:32])=[CH:23][C:22]=4[CH2:21]3)=[O:19])[CH2:11][C@H:10]([NH:9][C@H:8]3[CH2:7][CH2:6][O:5][CH2:4][C@H:3]3[O:2][CH3:1])[CH2:17][C@H:13]2[CH2:14]1)\[NH2:38])#[N:36]

Participants

6

Reactant 2

HCID 4350929Sodium dicyanamideHCID 86708896((3aR,5R,6aR)-5-(((3S*,4S*)-3-Methoxytetrahydro-2H-pyran-4-yl)amino)octahydro-cyclopenta[c]pyrrol-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

Product 1

HCID 178496720HCID 178496720, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of Example 1 (HCl salt, 50 mg, 0.0865 mmol), sodium dicyanamide (10.32 mg, 0.116 mmol) in 5% water in i-PrOH (1.2 mL) in a sealed tube was flushed with Ar and heated at 120° C. for 5 h. After cooling to rt, the mixture was diluted with DCM, filtered and evaporated. The residue was purified by CombiFlash (eluent: 10% 7N NH3 in methanol in DCM) to give the product as a colorless gel. 1H-NMR (400 MHz, CDCl3): δ 1.54-1.92 (m, 5H), 2.37 (br. s., 1H), 2.71 (br. s., 1H), 3.07-4.23 (m, 19H), 4.66-4.96 (m, 2H), 5.80 (m, 2H), 7.73 (s, 1H), 8.71 (br. s., 1H); LC/MS: C25H32F3N7O3: m/z 536.2 (M+H).

Workup

  1. temperatureAfter cooling to rt
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue was purified by CombiFlash (eluent: 10% 7N NH3 in methanol in DCM)

Sources & evidence

ORD record
ord-c3a66e4e2b5b4cce9976f297355ac063
Source dataset
uspto-grants-2015_05
Patent number
US09024017B2

Reaction notes

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