Diisopropylethylamine → HCID 178495691, compound

HRID 1751726Notes

Reaction equation

HRID 1751726 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][NH:7][C@H:6]([C:9]2[NH:10][C:11]([C:14]3[CH:19]=[C:18]4[CH2:20][O:21][C:22]5[CH:53]=[C:52]6[C:25]([CH:26]=[CH:27][C:28]7[N:32]=[C:31]([C@@H:33]8[CH2:37][CH2:36][CH2:35][N:34]8[C:38](=[O:51])[C@H:39]([NH:46][C:47](=[O:50])[O:48][CH3:49])[C:40]8[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=8)[NH:30][C:29]=76)=[CH:24][C:23]=5[C:17]4=[CH:16][CH:15]=3)=[CH:12][N:13]=2)[CH2:5]1.[CH3:54][O:55][C@H:56]([CH3:66])[C@H:57]([NH:61][C:62]([O:64][CH3:65])=[O:63])[C:58](O)=[O:59].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>CN(C=O)C>[CH3:65][O:64][C:62]([NH:61][C@H:57]([C:58]([N:7]1[CH2:8][C@@H:4]([CH2:3][O:2][CH3:1])[CH2:5][C@H:6]1[C:9]1[NH:10][C:11]([C:14]2[CH:19]=[C:18]3[CH2:20][O:21][C:22]4[CH:53]=[C:52]5[C:25]([CH:26]=[CH:27][C:28]6[N:32]=[C:31]([C@@H:33]7[CH2:37][CH2:36][CH2:35][N:34]7[C:38](=[O:51])[C@H:39]([NH:46][C:47](=[O:50])[O:48][CH3:49])[C:40]7[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=7)[NH:30][C:29]=65)=[CH:24][C:23]=4[C:17]3=[CH:16][CH:15]=2)=[CH:12][N:13]=1)=[O:59])[C@@H:56]([CH3:66])[O:55][CH3:54])=[O:63]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59540170(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acidHCID 178495707HCID 178495707, compound

Product 1

HCID 178495691HCID 178495691, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl {(1R)-2-[(2S)-2-(9-{2-[(2S,4S)-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate (51 mg, 0.072 mmol), (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid (14 mg, 0.072 mmol), HATU (30 mg, 0.079 mmol) and 0.4 mL 10% DIPEA in DMF was stirred at room temperature for 1 hour. The product was purified by reverse phase HPLC. The product was converted to the free base by dissolution in 2 mL 1:1 acetonitrile:methanol and passage through a prepacked cartridge of polymer supported carbonate. The eluent was concentrated, taken up in 1% TFA in 1:1 acetonitrile:water, frozen, and lyophilized to give the product as a trifluoroacetate salt. (24 mg)

Workup

  1. customThe product was purified by reverse phase HPLC
  2. dissolutionThe product was converted to the free base by dissolution in 2 mL 1:1 acetonitrile
  3. concentrationThe eluent was concentrated
  4. temperaturewater, frozen

Sources & evidence

ORD record
ord-a3dd3a2b71264699bb428f63207bf111
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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