Diisopropylethylamine → HCID 178495690, compound

HRID 1412999Notes

Reaction equation

HRID 1412999 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:56]([NH:58][C@@H:59]([CH:63]([CH3:65])[CH3:64])[C:60](O)=[O:61])=[O:57].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>[CH3:54][O:55][C:56](=[O:57])[NH:58][C@@H:59]([CH:63]([CH3:64])[CH3:65])[C:60]([N:40]1[CH2:41][C@@H:42]([CH2:44][O:45][CH3:46])[CH2:43][C@H:39]1[C:37]1[NH:38][C:34]([C:29]2[CH:30]=[C:31]3[CH2:32][O:33][C:20]4[CH:19]=[C:18]5[C:23]([CH:24]=[CH:25][C:15]6[N:14]=[C:13]([C@@H:9]7[CH2:10][CH2:11][CH2:12][N:8]7[C:6](=[O:7])[C@H:5]([NH:4][C:3]([O:2][CH3:1])=[O:53])[C:47]7[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=7)[NH:17][C:16]=65)=[CH:22][C:21]=4[C:26]3=[CH:27][CH:28]=2)=[CH:35][N:36]=1)=[O:61]

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 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 178495707HCID 178495707, compound

Product 1

HCID 178495690HCID 178495690, 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 (55 mg, 0.077 mmol), (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (14 mg, 0.077 mmol), HATU (32 mg, 0.085 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. (30.7 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-5667436396384202b37a37c10188e46f
Source dataset
uspto-grants-2014_12
Patent number
US08921341B2

Reaction notes

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