Diisopropylethylamine → HCID 178495691, compound

HRID 1413000Notes

Reaction equation

HRID 1413000 reaction equation
[CH3:1][O:2][C:3](=[O:53])[NH:4][C@H:5]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:17][C:16]2[C:18]3[C:23]([CH:24]=[CH:25][C:15]=2[N:14]=1)=[CH:22][C:21]1[C:26]2[C:31]([CH2:32][O:33][C:20]=1[CH:19]=3)=[CH:30][C:29]([C:34]1[NH:38][C:37]([C@@H:39]3[CH2:43][C@H:42]([CH2:44][O:45][CH3:46])[CH2:41][NH:40]3)=[N:36][CH:35]=1)=[CH:28][CH:27]=2)=[O:7].[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>[CH3:1][O:2][C:3](=[O:53])[NH:4][C@H:5]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:17][C:16]2[C:18]3[C:23]([CH:24]=[CH:25][C:15]=2[N:14]=1)=[CH:22][C:21]1[C:26]2[C:31]([CH2:32][O:33][C:20]=1[CH:19]=3)=[CH:30][C:29]([C:34]1[NH:38][C:37]([C@@H:39]3[CH2:43][C@H:42]([CH2:44][O:45][CH3:46])[CH2:41][N:40]3[C:58](=[O:59])[C@H:57]([C@@H:56]([CH3:66])[O:55][CH3:54])[NH:61][C:62]([O:64][CH3:65])=[O:63])=[N:36][CH:35]=1)=[CH:28][CH:27]=2)=[O:7]

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, the 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-b5db951fc9f2423fa640265479c32add
Source dataset
uspto-grants-2014_12
Patent number
US08921341B2

Reaction notes

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