Diisopropylethylamine → HCID 67281619, compound

HRID 446964

Reaction equation

HRID 446964 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:38])[CH:9]([CH3:37])[C:10]([NH:12][CH:13]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:14]([N:16]1[CH:23]2[CH:19]([N:20]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:21][CH:22]2[C:24]([OH:26])=O)[CH2:18][CH2:17]1)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C@H:72]1([NH2:82])[C:81]2[C:76](=[CH:77][CH:78]=[CH:79][CH:80]=2)[CH2:75][CH2:74][CH2:73]1>CN1C(=O)CCC1.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[N:8]([CH:9]([C:10](=[O:11])[NH:12][CH:13]([CH:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1)[C:14]([N:16]1[CH2:17][CH2:18][CH:19]2[N:20]([S:27]([CH3:30])(=[O:28])=[O:29])[CH2:21][CH:22]([C:24](=[O:26])[NH:82][CH:72]3[C:81]4[C:76](=[CH:77][CH:78]=[CH:79][CH:80]=4)[CH2:75][CH2:74][CH2:73]3)[CH:23]12)=[O:15])[CH3:37])[CH3:38])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 70580721-Aminotetralin, (R)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67280901HCID 67280901, compound

Product 1

HCID 67281619HCID 67281619, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A solution of crude 21 (106 mg, 0.19 mmol) in NMP (5 mL) was cooled to 0° C. and treated with HATU (73 mg, 0.19 mmol) and DIPEA (0.1 mL, 0.57 mmol). After 10 min, (1R)-1,2,3,4-tetrahydro-naphthalen-1-ylamine (0.05 mL, 0.35 mmol) in NMP (3 mL) was added. The reaction was allowed to warm to ambient temperature. After 16 h, the solution was diluted with EtOAc, washed successively with 1M HCl, brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 22 which was used without further purification. Mass spectrum, m/z [688.5] (M+H)+.

Workup

  1. waitAfter 16 h
  2. washwashed successively with 1M HCl, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b3daea1956ff4f86bf1584ccf8fb951d
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Linked notes

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