Water → {(1S,2R)-2-[5-(3-Methyl-1H-indol-7-ylamino)-4-oxo-3,4-dihydro-pyrido[3,4-d]pyridazin-7-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

HRID 629203Notes

Reaction equation

HRID 629203 reaction equation
Cl[C:2]1[N:12]=[C:11]([NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[C:19]3[CH3:23])[C:5]2[C:6](=[O:10])[NH:7][N:8]=[CH:9][C:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.[NH2:33][C@@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@@H:35]1[NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44].O>CN1C(=O)CCC1>[C:43]([O:42][C:41](=[O:47])[NH:40][C@H:35]1[CH2:36][CH2:37][CH2:38][CH2:39][C@H:34]1[NH:33][C:2]1[N:12]=[C:11]([NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[C:19]3[CH3:23])[C:5]2[C:6](=[O:10])[NH:7][N:8]=[CH:9][C:4]=2[CH:3]=1)([CH3:46])([CH3:44])[CH3:45]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 899724117-Chloro-5-((3-methyl-1H-indol-7-yl)amino)pyrido[3,4-d]pyridazin-4(3H)-one

Product 1

HCID 89972453{(1S,2R)-2-[5-(3-Methyl-1H-indol-7-ylamino)-4-oxo-3,4-dihydro-pyrido[3,4-d]pyridazin-7-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To 7-chloro-5-(3-methyl-1H-indol-7-ylamino)-3H-pyrido[3,4-d]pyridazin-4-one (177 mg, 0.543 mmol) in NMP (1 ml) in a sealable glass vial, was added DIPEA (0.190 ml, 1.087 mmol) and tert-butyl(1S,2R)-2-aminocyclohexylcarbamate (233 mg, 1.087 mmol). The vial was capped to close and the reaction mixture was heated on a sandbath at 120° C. for 3 days. The resulting mixture was poured into water (20 ml), and extracted with EtOAc (20 ml). The organic phase was washed with water and brine, dried over Na2SO4, then concentrated under vacuum. The residue was triterated with DCM, then collected by filtration and dried to give a gummy solid.

Workup

  1. customThe vial was capped
  2. customto close
  3. extractionextracted with EtOAc (20 ml)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. filtrationcollected by filtration
  8. customdried
  9. customto give a gummy solid

Sources & evidence

ORD record
ord-feb174bf91304501956921b59a935653
Source dataset
uspto-grants-2016_04
Patent number
US09315500B2

Reaction notes

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